October 2011 - Organic Reactions Wikiorganicreactions.org/images/a/af/ManuscriptGuide_2012.pdfORGANIC REACTIONS MANUSCRIPT GUIDE Overview This document provides guidelines for the

ORGANIC REACTIONS

Editorial Board

Manuscript Guide

October

2011

ORGANIC REACTIONS

MANUSCRIPT GUIDE

Overview

This document provides guidelines for the preparation, submission, and publication of a

chapter for Organic Reactions. Supplementary electronic files including a Microsoft® Word

template for the text, ChemDraw® stationery files containing the default settings for tables and

text graphics, and an EndNoteTM template are also provided to the s via e-mail. All of these

documents are available online at

http://onlinelibrary.wiley.com/book/10.1002/0471264180/homepage/ForAuthors.html.

Insofar as Organic Reactions is an ongoing series, style guidelines are less flexible than

those for most journals. Our general style conventions parallel those of The ACS Style Guide,†

and authors should use that reference as a supplement to this Manuscript Guide. However, our

graphics styles are very precise and authors must apply the styles described herein to all

structures and equations.

One of the most valuable features of Organic Reactions is the Tabular Survey that lists all

examples of the chapter’s subject reaction that the author(s) has been able to find in the

literature. Because of the complexity of the Tabular Survey and the production requirements of

our publisher, authors are required to prepare table entries using ChemDraw software following

carefully established guidelines. (A Power Point tutorial on table preparation resides at the web

address given above.) These entries will be compiled into the Tabular Survey by the typesetter

through our publisher, John Wiley & Sons, once the chapter draft has been approved.

Authors’ principal contacts with Organic Reactions during chapter preparation are the

responsible members of the Editorial Board assigned to them at chapter initiation. Authors

should keep their Editors apprised of their progress, as well as of any problems that arise, on a

quarterly basis. Authors should also become familiar with the sequence of chapter preparation

and review as described beginning on page 3.

The end result of the painstaking preparation of such manuscripts is a publication of

consistently high quality that continues to serve as a principal reference series. We are grateful to

participating authors who help to maintain the high caliber of Organic Reactions.

The Editorial Board of Organic Reactions

October 1, 2011

† Coghill, A. M.; Garson, L. R. The ACS Style Guide, A Manual for Authors and Editors, 3rd ed., American Chemical

Society: Washington, DC, 2006.

i

Contents

REQUIREMENTS FOR FINAL MANUSCRIPT SUBMISSION ................................................ 1!

INTRODUCTION .......................................................................................................................... 3!

PREPARATION OF THE CHAPTER ........................................................................................... 3!

THE MANUSCRIPT ...................................................................................................................... 4!

ORGANIZATION OF THE CHAPTER ........................................................................................ 4!

Title Page .................................................................................................................................... 4!

Abstract ....................................................................................................................................... 5!

Order of Subject Headings .......................................................................................................... 5!

STYLE CONVENTIONS USED IN THE TEXT .......................................................................... 8!

Introduction Through Experimental Conditions Sections .......................................................... 8!

General Text Conventions ...................................................................................................... 8!

Numbering Compounds and Text Graphics ........................................................................... 9!

Experimental Procedures Section ............................................................................................. 10!

FORMULAS AND STRUCTURES ............................................................................................ 11!

Formulas ................................................................................................................................... 11!

Group Abbreviations and Symbols ........................................................................................... 11!

Structures .................................................................................................................................. 13!

TEXT GRAPHICS (EQUATIONS, SCHEMES, FIGURES) ...................................................... 14!

ABBREVIATIONS ...................................................................................................................... 15!

REFERENCES ............................................................................................................................. 16!

Coding and Inserting ................................................................................................................. 16!

Style .......................................................................................................................................... 17!

Journal References ................................................................................................................ 17!

Books .................................................................................................................................... 19!

Unpublished Results ............................................................................................................. 19!

Personal Communications .................................................................................................... 19!

Patents ................................................................................................................................... 19!

TABLES ....................................................................................................................................... 20!

Table Format ............................................................................................................................. 21!

General Instructions .............................................................................................................. 21!

Table Columns ...................................................................................................................... 23!

Sub-Tables ............................................................................................................................ 24!

ii

Footnotes ............................................................................................................................... 26!

EDITING THE MANUSCRIPT ................................................................................................... 26!

APPENDIX I: Equation Files and Insertion Numbers ................................................................ 27!

Sample ChemDraw Equations File Showing Insertion Numbers (top left corner) .................. 28!

Sample Text with Equation Insertion Numbers ........................................................................ 29!

APPENDIX II: Guidelines for Computer-Drawn Text Graphics ................................................ 30!

Annotated Example of Text Equation ...................................................................................... 33!

APPENDIX III: Guidelines for Computer-Drawn Tables ............................................................ 34!

Construction of Sub-Tables ...................................................................................................... 38!

Sample Table Files .................................................................................................................... 38!

APPENDIX IV: Use of EndNote! for Tracking Table References ........................................... 41!

APPENDIX V: The Journal of Organic Chemistry Standard Abbreviations and Acronyms ...... 43!

APPENDIX VI: Copy Editing and Proofreading Symbols ......................................................... 46!

1

REQUIREMENTS FOR FINAL MANUSCRIPT SUBMISSION

This section summarizes what the final product for an Organic Reactions chapter should

look like. The Organic Reactions Manuscript Guide is an essential resource that explains how to

get to this submission stage. Please read it carefully and direct any questions to your

Responsible Editor or the Editorial Coordinator.

The completed manuscript should be submitted electronically and include the following

components. A hard copy of all files must accompany the electronic version. The tables are to be

submitted as the galleys provided by Wiley, with any corrections or other revisions clearly

marked on the hard copy.

1. Abstract. The online version of the Organic Reactions chapter will include an abstract. The

author should submit an abstract and key words to the Responsible Editor with the final copy of

the chapter.

2. A Single MS Word File of the Manuscript. There should not be multiple Word files

corresponding to each section. The “manuscript” is the chapter text including the following

sections unless the Responsible Editor has agreed upon their exclusion.

Title Page (title of chapter, authors’ names and addresses)

Contents (page numbers unnecessary; headings should agree with those in the text and

Tables)

Acknowledgments (optional)

Introduction

Mechanism and Stereochemistry

Scope and Limitations

Applications to Synthesis (optional)

Comparison with Other Methods

Experimental Conditions (general overview, caution for hazardous procedures)

Experimental Procedures (in proper format; consult a recent volume of OR)

Tabular Survey (explanation of Tables, list of abbreviations)

2

Insertion numbers should be used where text equations, figures, or schemes belong. If

EndNote has been used to track references, the manuscript should contain the unformatted

citations. Formatting will be done upon finalization of the chapter.

3. Text Graphics. This folder should have multiple ChemDraw files containing equations,

figures, and schemes that are to be inserted into the body of the text. Representative equations

should indicate isolated yields as opposed to percent conversions, or yields determined by

spectroscopic methods. Multiple entries may be included on a single file page. Each entry should

be assigned a unique insertion number determined by its order of appearance in the text. (For

example, if Scheme 1 follows Eq. 10 in the text, its insertion number should be the next in

sequence after that used for Eq. 10.) Insertion numbers (in sequence) should be clearly marked in

the upper left corner. ChemDraw files should be named based on the first insertion number

appearing on that file (e.g., TxGr 001-, TxGr 005-, and so on). (See Appendix I of the Organic

Reactions Manuscript Guide for sample pages.)

4. References.

A. If EndNote™ has been used, this file should be the EndNote Library. Print an EndNote

bibliography as a hard copy for review.

B. Otherwise, a reference list in OR style as a single Word file. At this stage, the Table

references should still be coded. Either the Editorial Coordinator or the author will enter

the final numbers into the Tables, and will generate the final, correctly numbered,

reference list.

5. Tables. The tables should be submitted as the galley files compiled by Wiley. Any additions,

deletions, corrections, or other revisions should be clearly marked on the hard copy.

3

INTRODUCTION

An Organic Reactions chapter is a critical analysis of a reaction, aimed at providing

guidance to a synthetic chemist who wishes to carry out the reaction. Because Organic Reactions

is a continuing series, we try to maintain a consistent format for the organization of chapters and

a consistent style for chemical equations and structures. Although we use many of the style

conventions of The ACS Style Guide, the flexibility that the ACS journals permit in writing

chemical formulas, equations, and structures is not suitable for a monograph series, and authors

should use the conventions given in this Guide. Any recent volume of Organic Reactions can

serve as an example for preparation of chapters.

Authors are required to submit text equations and table entries as electronic files prepared

using ChemDraw†† (version 8.0 or higher, CambridgeSoft, Inc., 100 Cambridge Park Drive,

Cambridge, MA 02140; www.cambridgesoft.com). This requirement has been established to

reduce the time of editorial preparation and the number of errors caused by redrawing, given that

our publisher uses ChemDraw files.

PREPARATION OF THE CHAPTER

Several members of the Organic Reactions Editorial Board assist authors in their chapter

preparation and production. Each chapter is assigned to a Responsible Editor, who serves as

liaison with the author. The Responsible Editor is responsible for review of the manuscript and

for seeing that the chemistry is organized and presented according to Organic Reactions style

and format. In addition, the Editorial Coordinator checks that the manuscript, text graphics, and

tables are in accordance with Organic Reactions style and production requirements. Lastly, a

secretary to the Editorial Board checks the chapter in its entirety, then works with our publisher,

John Wiley & Sons, to manage chapter submission, page proofs, and publication.

The Responsible Editor will provide the author with a sample of an acceptable chapter

outline, and sample pages for each of the sections (manuscript, text graphics, references, and

tables). Based on these examples, authors must submit to the Responsible Editor a detailed

outline of the material they propose to cover, including a few key references. The author must

then submit sample pages of text, text graphics, and table entries once the chapter outline is

approved. It is essential that these pages be reviewed as early as possible to ensure that the

chapter will be formatted as required. Our experience shows that correcting departures from

Organic Reactions style and format at an early stage can save much time and labor in later

editorial revision, thus preventing publication delays.

†† Please note that ChemDraw, Microsoft, Microsoft Word, Macintosh, and Windows are all registered trademarks.

4

Once sample pages have been reviewed and approved, the author’s first task is to assemble,

organize, and compile the table entries according to the directions provided on page 21. Upon

completion, electronic copies of these files are sent to the Editorial Coordinator. If the format is

acceptable, the Editorial Coordinator holds these files until the first draft of the manuscript is

complete.

The manuscript draft is submitted to the Responsible Editor, who will distribute copies to

other editors (and occasionally to outside experts) for review, and then compile and relay their

comments back to the author. When the Responsible Editor approves the chapter draft, including

the described organization and content of the tables, the Editorial Coordinator commences

processing the table entries, and sends the vetted files to Wiley. Wiley in turn transfers the files

to the typesetter, who assembles them into the properly formatted Tabular Survey. Completed

table galleys are ultimately returned to the author so that the chapter may be reviewed and

corrected in toto.

Both hard and electronic copies of the final manuscript, and marked table galley files, are

submitted to the Responsible Editor, who sends copies of these to the Editorial Coordinator.

The program ChemDraw, version 8.0 or higher, is required to prepare text graphics and

tables entries for the chapter. If authors do not have access to ChemDraw, Organic Reactions

will supply this program. Authors must avoid using a mixed ChemDraw/Microsoft Word format,

other mixed formats, or the poster (multi-page) ChemDraw setting to prepare tables entries or

text graphics, because our compositor cannot work with such files.

THE MANUSCRIPT

The text portion of the manuscript should be prepared as “US Letter” using 12-pt Times or

Times Roman font, double line-spacing, and 0.75 in. (19 mm) left-justified margins. A Word

template with the proper settings will be provided by e-mail and is also available online at

http://onlinelibrary.wiley.com/book/10.1002/0471264180/homepage/ForAuthors.html. Specific

instructions for preparation of entries to be included in the Tabular Survey are provided on page

21 and in Appendix III.

ORGANIZATION OF THE CHAPTER

Title Page

This page includes the title of the chapter, the authors’ full names, starting with the

corresponding author, and the corresponding author’s affiliation and address (in English)

including the zip code and zip code extensions, and e-mail address. All information should be in

English.

5

Abstract

The abstract is for use only with the online version of the chapter. It should provide

sufficient information to characterize the subject reaction and the scope of the coverage.

Order of Subject Headings

CONTENTS

List all headings and subheadings used in the text, all Experimental Procedures, and

numbers and titles of all Charts and Tables in the Tabular Survey. Do not include page numbers.

ACKNOWLEDGMENTS

(Optional)

INTRODUCTION

The objective of Organic Reactions is to provide a reference work and critical commentary

on a reaction. Accordingly, neither a chronological development nor early history of the reaction

should be included.

The reaction should be defined and illustrated. Historical background, if any, should be

brief. Indicate the scope of and limitations to the coverage. Give references to any previous

reviews of the reaction.

MECHANISM AND STEREOCHEMISTRY

Give a brief discussion of current ideas about the mechanism of the reaction and of any

stereochemistry involved. Historical development of these topics should be avoided. Provide the

kind of information that will help a chemist select conditions for using the reaction effectively.

These subjects may be separated into two sections if so desired.

SCOPE AND LIMITATIONS

This section is the backbone of the text discussion. It should comprise a critical analysis of

the current status of the reaction, rather than a running catalog of literature reports. All phases of

the reaction should be illustrated with equations and product yields. Include in this section:

• Currently known limitations on the scope of the reaction; and

• Suggestions for new applications or extensions of the reaction.

APPLICATIONS TO SYNTHESIS

If appropriate, a few examples of important syntheses in which the reaction has been used

may be included (optional).

6

COMPARISON WITH OTHER METHODS

Summarize advantages and disadvantages of the reaction in comparison with other routes

to the same products.

EXPERIMENTAL CONDITIONS

Comment on preferred catalysts, solvents, and conditions for using the reaction. Describe

any unusual techniques for handling reagents or isolating products. Include comments on

significant hazards and safety precautions. If a particularly hazardous reagent, product, or

byproduct is involved, provide a laboratory procedure for destroying it.

EXPERIMENTAL PROCEDURES

Provide examples of the reaction taken from the literature. Include enough procedures to

illustrate significant applications and variations of the reaction, being selective so as to minimize

redundancy. Select examples that provide the most detailed description of the experiment for that

example, including representative yields and thorough characterization of the products. An

equation showing the transformation should be included above the procedural description.

Relevant Organic Synthesis procedures can be included as a reference to the primary source.

Style conventions for this section are given on page 10.

TABULAR SURVEY

Begin with an introduction that describes the organization of the Tabular Survey, the cutoff

date for the literature survey, and any unusual conventions used in the Tables. List which

structural elements are not included in the carbon count of the substrate. Provide a list of

abbreviations used in the Tables (see any recent Organic Reactions chapter for examples). Note

that JOC-approved abbreviations (Appendix V) should not be included. The Responsible Editor

should approve uncommon abbreviations in advance.

The introduction is followed by a Tabular Survey of all examples of the reaction that can

be found in the literature. The survey should be current; that is, examples should be included

from literature dated within six months of the submission date. The format and conventions used

in the Tables are discussed starting on page 20.

REFERENCES

List all literature references cited in the chapter. See page 17 for the correct format.

Organic Reactions can provide assistance to authors with searches and in collecting

literature references. Authors who do not have access to SciFinder Scholar should provide a list

of index terms, key words, and/or compound names under which pertinent references might be

found by a computer search of Chemical Abstracts. Complete citations to several important

7

articles or reviews on the subject reaction should also be supplied. Literature references not

common to most US-based libraries may be submitted as a special request. All requests for

literature searches or reference copies should be sent to:

Dr. Linda S. Press

Phone: (845) 279-0623; e-mail: [email protected]

Organic Reactions can also assist authors in obtaining copies of patents, if necessary. Send

your Responsible Editor the following information: country, patent number, year of issue,

inventor (if available), assignee, and Chemical Abstracts reference. Your editor will arrange to

get a copy of the patent or the U.S. equivalent of a foreign patent, if available.

* * * * * * * * *

The following example shows the arrangement and format for a heading (Scope and

Limitations) with three subheadings.


Reductive Desulfonylation

Reductive Desulfonylations by Active Metals and Salts. (Text follows on

same line.) A major disadvantage of the use of metals and their salts, particularly on a

large scale…

Use of Alkali Metals in Ammonia. (Text follows on same line.) The reductive

desulfonylation process with…[Use only if needed]

The following example shows the correct arrangement and format for four subheadings

after the heading. Should more than four subheadings be required, please contact the Editorial

Coordinator.


Grignard-Derived Organocopper Reagents

Copper-Catalyzed Reactions of RMgX [Do not use unless you need more than four

levels of subheadings.]

(Begin text, if any, on new line.)

8

Substitution Reactions. (Text follows on same line.) The pros and cons of

using Grignard…

Epoxides. (Text follows on same line.) Ring opening of epoxides can be

achieved…

STYLE CONVENTIONS USED IN THE TEXT

Introduction Through Experimental Conditions Sections

General Text Conventions

• Use the present tense except for the few occasions where a historical connotation is

essential.

• Limit citation of chemists’ names to those who discovered the reaction or an important

modification of it. Exclude dates.

• When using commas to separate a series, include a comma before the “and”, e.g.,

“…reactions of aldehydes, ketones, and esters.”

• Use an en-dash rather than a hyphen in numerical ranges, e.g., 12–14 hours, 0–78°, etc.,

and to represent a chemical bond, e.g., N–H, C–O, etc.

• Set the prefixes bis, tris, and tetrakis in Roman and do not separate them from the

chemical name or formula unless followed by a Greek letter or a number.

• Refer to The ACS Style Guide for hyphenation rules. Do not hyphenate foreign phrases

even when used as compound adjectives.

transition-metal-promoted

Lewis acid catalyzed (no hyphens when a modifier is a proper name)

in situ generated

• Unlike the convention given in The ACS Style Guide, always use italic type for positional,

stereochemical, configurational, and descriptive structural prefixes whether or not they

appear with the chemical name or formula.

Examples:

cis-isomer

trans-alkenes

cis-propenyl isomer

cis-propenylcyclohexane

"…the hydrogens at the ring fusion have a cis relationship."

(R), (S), (Z), and (E) are always italicized and in parentheses.

(R)- and (S)-isomers

9

(Z)-isomer, (E)-isomer

(Z)-alkenes

(3R)-azide

(4R)-3,4-dimethyl-4-phenylhexan-2-one

(R)-21, where the bold number represents a specific compound.

(E,E)/(E,Z)/(Z,Z) = 45:43:12

• Unlike the convention given in The ACS Style Guide, always use italic type for element

symbols denoting attachment to an atom or site of ligation, and when used as an adjective or noun denoting a type of reaction.

N-acetyl

N-acetylation

• In general, use names, not formulas, for common chemicals in the text. However, if a

common chemical with a long name is mentioned frequently, a trivial name or acronym

can be used; it should be defined at the first use, for example:

diglyme (diethylene glycol dimethyl ether)

HMPA (hexamethylphosphoric triamide)

• Formulas of complex chemicals can be used instead of their names:

LiAlH(Ot-Bu)3 rather than lithium tri(tert-butyloxy)aluminum hydride.

Numbering Compounds and Text Graphics

• Text graphics (equations, schemes, figures) and structures should be included in the text

to facilitate review, but must be entered after an insertion number. The ChemDraw files

for these graphics must be provided as well. Multiple text graphics should be entered on a

given page, i.e., it is not necessary to have a separate ChemDraw file for each graphic. It

is essential to assign an insertion number to each graphic in the ChemDraw file, and to

use these numbers in the text, as described above, to indicate their proper placement (see

page 2 for insertion number protocol). Before submission to our publisher, the graphics

will be removed from the text leaving only the insertion numbers. See Appendix I for

(S)

(S)N3

(S)BnO

BnO

CO2H

NHBoc

R

(–)-menthyl

(–)-bornyl

(–)-isobornyl

(13)

(49)

(41)

(2S)/(2R)

1:1

1:1

1:1

10

examples of a ChemDraw file with equations and a text file with the corresponding

insertion numbers and graphics.

• If the discussion requires reference to a compound in a text graphic, identify the

compound with a boldface Arabic numeral and use the same boldface numeral in the

text. The number should be used with a descriptive noun; it should be in parentheses only

if the compound is completely named, for example:

keto ester 13, 3-methylcyclohexanone (25)

• Do not number every compound - only those that will facilitate the discussion. Compound

numbers should be in numerical sequence, beginning with the number 1.

• Do not give a compound more than one number in the chapter text. Likewise, avoid using

a single number to refer to derivatives of the same structure. (Note: If charts are used at

the beginning of the Tabular Survey to depict structures of ligands, catalysts, or other

reagents that are indicated by bold numbers in the tables, those numbers must also begin

with 1 and continue in sequence. Thus, it is unlikely that the assigned numbers will agree

with numbers for the same structures in the text, since charts often include additional

compounds not introduced in the text.)

• Assign numbers to text equations in sequence and write them as (for example) "Eq. 5" in

the text and as "(Eq. 5)" beside or beneath an equation. Treat schemes and figures

similarly.

• Use tables in the text only if essential.

• Identify tables in the text with capital letters (e.g., Table A) to distinguish them from the

Tabular Survey Tables. Figures should be numbered (e.g., Figure 1). The letter or

number is followed by a period and a short title in Roman, not bold.

• Avoid reference citations in text tables.

Experimental Procedures Section

• Begin each Experimental Procedure with an equation that illustrates the reaction,

followed by a header that defines the reaction in the following format:

Methyl 3-Amino-2-thioformylcrotonate (Thioformylation of an Enamine).30 A

solution of POCl3 (0.5 mL, 5.5 mmol) in DMF (1.5 mL) was added…

• Use the past tense.

• Use formulas for common reagents such as Et2O, EtOAc, THF, DMF, DMSO, CH2Cl2,

CHCl3, etc., rather than full chemical names.

• Give actual and percent yields and important physical constants of the product. Present

physical and spectroscopic data on products in the format of a recent volume of Organic

Reactions, based on that used in the Journal of Organic Chemistry. Put the data in the

order: mp or bp, chromatography data, specific rotation, IR, 1H NMR, 13C NMR, mass

11

spectra, quantitative analysis. Keep NMR data consistent for all procedures using either

ascending or descending order for chemical shift values.

• Omit the "C" in Celsius temperatures. Write Kelvin temperatures without the ° sign: 197

K.

FORMULAS AND STRUCTURES

The following guidelines apply to formulas and structures of starting materials and

products in both text and Tables.

Formulas

USE DO NOT USE

Me, Et, i-Pr, t-Bu CH3, CH3CH2, (CH3)2CH, (CH3)3C, iPr, tBu

n-C6H13 CH3(CH2)5

Ph !

4-MeC6H4 4-MePh (Ph = C6H5 only)

3-Cl-5-MeC6H3 The o, m, p notation for multiple substituents

• Be consistent with usage throughout the chapter (text and Tables).

Group Abbreviations and Symbols

• Lists of abbreviations can be found in The ACS Style Guide, and a list of approved

abbreviations published by the Journal of Organic Chemistry is available at

http://pubs.acs.org/userimages/ContentEditor/1218717864819/joceah_abbreviations.pdf

and is reproduced in Appendix V. (See also page 15 of this Guide.) • Define only those abbreviations that do not appear on the JOC list.

• Use of common abbreviations for functional groups, such as “Ac” for acetyl and “Bn” for

benzyl, is recommended.

• If it is necessary to save space or relieve crowding, formula designations for common

cyclic and heterocyclic rings can be used:

c-C5H9 for cyclopentyl C4H3O for furyl

c-C6H11 or Cy for cyclohexyl C4H3S for thienyl

C10H7 or Np for naphthyl C5H4N or Py for pyridyl

12

• Use the generic symbols:

R1, R2, R3, etc. (not R1, R2, R3, etc.)

Ar for aryl

X for halogen, HX for halogen acid

Y, Z for other generics, such as nucleophiles or leaving groups

• Except for captions defining “R–” groups, use line drawings, not linear formulas, in

Tables.

• Place isomer indicators before a substituent.

• Use numeric (2-, 3-, 4-) isomer indicator systems.

• Do not use charge signs on simple salts. Use charge signs, not circled, on complex salts.

Do not use the charge symbols provided by ChemDraw; use a superscripted ‘en-dash’

(“option-hyphen” on a Macintosh) for a negative charge; a positive charge is simply the

superscripted ‘plus’ key.

(n-C8H17)3B–Me Li+t-BuOK

• Use the ‘en-dash’ for negative numbers and optical rotations, e.g. –20°.

• The following Mac shortcuts are useful for creating some commonly used symbols and

signs:

Symbol Mac Shortcut Example

º option-shift-8 or option-0 78°

• option-8 BF3•OEt2

- hyphen N-acetyl, t-Bu

– option-hyphen 0–78°, 32–54% ee, hexane–ether solvent

— option-shift-hyphen (—)

" symbol font a "-keto ester

# symbol font b #-keto ester

Å option-shift-A 4 Å MS

• PC users can locate the above characters in the Character Map window of ChemDraw.

Select Times New Roman font, not Symbol, when selecting a character to insert.

t-Bu i-PrAr = 2-MeO-4-HOC6H3

OHNOT (E)-CH3CH(CH3)CH=CH(CH2)3CH2OH

13

Structures

All text graphics and Tables must be computer drawn using ChemDraw version 8.0 or

higher. The ChemDraw preference settings are shown in Appendix II for text graphics and

Appendix III for table entries, and are the default settings for the two ChemDraw stationery files:

OR TxGr Stationery 2012.cds and OR Table Stationery 2012.cds provided as part of the

materials to assist chapter preparation. Please note that the text settings differ. Organic Reactions

conventions for computer-drawn structures follow.

• Wherever possible, maintain a similar orientation between the structure(s) of the starting

material(s) and the structure(s) of the product(s).

• Use the ‘open bond’ to represent methyl when attached to a carbon atom in a structure.

Use ‘–Me’ when a methyl group is attached to a non-carbon atom. Small or easily

abbreviated “R” substituents may be part of the atom label (no drawn bond), if preferred.

Vertically aligned atom labels require a line spacing of 10 pts in text graphics and 9 pts in

table entries.

• Use Kekulé bonds in aromatic rings. The inscribed circle or ellipse should be used only

for ions, complexes, and ferrocene-type compounds.

• Use the regular pentagon, not the "log cabin," for 5-membered rings.

• Set 6-membered and heterocyclic rings on a ring point; set other rings on a base. This

orientation may be modified if the structure is complex and the rings are not involved in

the chemical transformation.

Br

H

O

N

Me

NMe

text formula, 10 pt

table formula, 9 pt

line spacing

NOT

O

BrNH2O

14

• Direct bonds to rings as nearly as possible toward the center of the regular polygon unless

crowding makes this impossible. (Clicking with the ChemDraw bond tool on an atom in a

ring will automatically put the new bond in the correct orientation.)

• Hydrocarbon substituents on the left sides of rings should be drawn in the direct form.

Other substituents should be drawn to show the mode of attachment.

• Do not use solid dots or bar lines to denote configuration at ring junctions. Organic

Reactions denotes configurations with the conventions shown in the decalol below,

although the stereostructure of sugars can be shown as in the following examples.

TEXT GRAPHICS (EQUATIONS, SCHEMES, FIGURES) • REFER TO APPENDIX II FOR THE CHEMDRAW SETTINGS USED FOR DRAWING

TEXT GRAPHICS, AND FOR AN ANNOTATED EXAMPLE.

• Text graphics should be selected so as to best illustrate the discussion in the text.

Representative equations should include isolated yields. Avoid using equations where

either percent conversions, or yields determined by spectroscopic methods, are the only

yields reported. Whenever possible, use “er” instead of “ee”, and specify absolute

configuration.

• Use the supplied ChemDraw file, OR TxGr Stationery 2012.cds, which has all the proper document settings and the correct page setup.

• The general text conventions given on page 8 apply to captions in the text graphics except where noted.

• Assign a unique insertion number to each equation, scheme, or figure and use that number to indicate the place of insertion of that graphic in the text (see Appendix I). Do not create separate files for the different types of graphics, but rather present them in order regardless of type. For example, graphic inserts 34–38 may comprise Eq. 34, Scheme 5, Figure 3, Eq. 35, and Eq. 36.

OH

O

O

O

OH

O

OH

HO

OH

OMe

HO

O

O

Ph

i-Prt-Bu

CF3 OH

H2N SHO3S n-C6H13n-C6H13

15

• The width of computer-drawn graphics must not exceed 7.25" (18.4 cm) when printed. If more space is needed, put a product or products on a second line, indented from the top line.

• Align equations and similar graphics horizontally. • Use the medium-headed arrow. • Scale structures drawn over arrows by 85%; do not scale atom labels. • Use abbreviations or acronyms for long chemical names over arrows. • Use "heat", not "$", but specify temperature whenever possible. • Do not use left-running arrows. • If a single example requires multiple equations (and arrows) to represent a series of

chemical transformations, label the entry as a scheme, not as an equation. Figures usually do not contain reaction arrows.

• Do not capitalize words over or under arrows. Equations or schemes that illustrate different results from different reagents or conditions should be drawn with orthogonal lines and arrows, rather than with slanted arrows.

ABBREVIATIONS • Lists of abbreviations can be found in The ACS Style Guide, and a list of approved

abbreviations published by the Journal of Organic Chemistry is available at http://pubs.acs.org/userimages/ContentEditor/1218717864819/joceah_abbreviations.pdf and is reproduced in Appendix V.

• Define only those abbreviations that do not appear on the JOC list. • Do not use a period after an abbreviation unless the abbreviation itself is an English word

or is a Latin expression. Latin abbreviations or expressions that are commonly used in English are not set in italics: e.g., etc., vs., in situ, via. Authors are encouraged to replace other Latin phrases with their English equivalents, e.g. “vide infra” with “later in the text” and so forth.

TMSCl

–5°(15%)

(75%)

h!, C6H6 heat xylene

138°

C

B

A

HMPA

15–20°

A B C D

16

• Use the following forms: IR GLC 4 Å MS equiv (text graphics); eq (tables) UV HPLC 2 N HCl mol, mmol, mol % 1H NMR TLC Na2SO4•10H2O rt (room temperature)

• Spell out units of time, “room temperature”, and “equivalents” in the text. • Abbreviate units of time (s, min, h, d), “room temperature” (rt), and equivalents (equiv)

in the text graphics and Experimental Procedures. • Abbreviate units of time (s, min, h, d), “room temperature” (rt), and equivalents (eq) in

the table entries. • Omit the "C" in Celsius temperatures (e.g., 36°). Write Kelvin temperatures without the ° sign: 197 K.

REFERENCES

Coding and Inserting

To aid in manuscript preparation, do not insert reference numbers in the text or table

entries until the chapter has been processed by the Editorial Coordinator. Editorial changes

often alter the numerical sequence of references if they are introduced too early in production.

Either the Editorial Coordinator will do the final numbering, or the author will be asked to do so

before the chapter goes to our publisher. • Use reference codes or EndNote citations in the text and table entries.

• Include only one citation per reference code.

• Avoid assigning more than one code to a single reference.

• Put reference citations in the text after any punctuation.

• Provide a list of the references prefaced with their assigned codes, and sorted

alphabetically according to those codes. If using EndNote, submit the EndNote library

complete with attendant data files.

There are several computer program reference managers that can be used during

manuscript preparation. Two commercial programs are EndNote% (Niles Software, 800 Jones

St., Berkeley, CA 94710; www.niles.com) and ProCite (Research Information Systems, 2355

Camino Vida Roble, Carlsbad, CA 92009; www.risinc.com). Both run on Macintosh and

Windows computers and have reference collection, organization, and formatting capabilities. See

Appendix IV for a suggested procedure using EndNote to facilitate Table reference organizing

and tracking.

Do not use the MS Word footnote/endnote feature for entering references in the

manuscript. For final processing, the references must be submitted as a separate list, and the field

codes removed from the text. There is no automatic way to do this with the Word feature as there

17

is with the EndNote software. Thus all footnote numbers must be overwritten manually, an

extremely time-consuming process.

Many authors have used an alternative alphanumeric system in which, e.g., an article by

Smith, Jones, and Richards, published in 1991 is coded SJ-91 (or SJR-91). Upon final

processing, these temporary codes are replaced with numbers and the bibliography is generated

in numerical order.

Style

For authors choosing to use EndNote™, an Organic Reactions Style template is available

from Linda Press, [email protected].

Journal References

Organic Reactions uses the inverted-name format used by the ACS journals, printing

authors' names, initials, journal, year, vol., page. Cite all authors; do not use et al. Use CASSI

journal abbreviations. The ACS Style Guide provides “CASSI Abbreviations for the 1000+ Most

Commonly Cited Journals” on pages 328–339. CASSI abbreviations are also accessible through

the RSC Publishing website:

http://www.rsc.org/publishing/resource/authorguidelines/authoringtools/journalabbreviations/ind

ex.asp).

When an English translation of a foreign language journal exists, cite the translation first

and include a citation to the original article, if possible. Chemical Abstracts citations for foreign

journal articles are optional.

Examples:

Vernon, J. M.; Ahmed, M.; Kricka, L. J. J. Chem. Soc., Perkin Trans. 1 1978, 837.

Rose, L. M.; Hyka, J. Ind. Eng. Chem. Process Des. Dev. 1984, 23, 429.

Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587.

Badami, B. V.; Puranik, G. S. Rev. Roum. Chim. 1975, 20, 981.

Brown, A. C. Ph.D. Dissertation, University of Massachusetts, 1984; Univ. Microfilms

Int., Order No. DA8410268.

Aksenov, A. B. J. Gen. Chem. USSR (Engl. Transl.) 1995, 65, 2050; Zh.

Obshch. Khim. 1995, 65, 2100.

18

Note these CASSI journal name abbreviation changes associated with

certain publication years:

J. Chem. Soc., Perkin Trans. 1 (1972–1999)

Perkin 1 (2000)


Org. Biomol. Chem. (2003–present)


Perkin 2 (2000)


Org. Biomol. Chem. (2003–)

J. Chem. Soc., Dalton Trans. (1972–1999)

Dalton (2000)

J. Chem. Soc., Dalton Trans. (2001–2002)

Dalton Trans. (2003–)

J. Chem. Soc., Chem. Commun. (up to and including 1995)

Chem. Commun. (1996–present)

Angew. Chem., Int. Ed. Engl. (up to and including 1997)

Angew. Chem., Int. Ed. (1998– present)

19

Books

The author's name(s) is followed by the book title, set in italics, followed by the edition,

editors, publisher, city of publication, year, and page number(s). Omit page numbers when

referring to the book in its entirety. A book that is part of a series is cited like a journal if it is so

listed in Chemical Abstracts.

Examples:

Cohn, E; Edsall, J. T. Proteins, Amino Acids, and Peptides; Reinhold: New York, 1943.

Noels, A. F.; Demonceau, A. In Applied Homogeneous Catalysis with Organometallic

Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996; pp 733–

747.

Johnson, J. R. In Organic Chemistry, 2nd ed.; Gilman, H., Ed.; Wiley & Sons: New

York, 1986; Vol. II, pp 1821–1864.

Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F.

G. H., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, p 509.

Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. 1989, 37, 57.

Smith, L. I. Org. Synth. Coll. Vol. 2 1943, 250.

Unpublished Results

Kapoor, R. P.; Garg, C. P.; Bhatti, S. P., Kurukshetra University, Kurukshetra,

Haryana, India, unpublished results.

Personal Communications

Use "personal" rather than "private." Include sufficient information about the person's

location to enable a reader to contact that person. Example:

Overman, L. E. Department of Chemistry, University of California, Irvine, Irvine, CA

92697. Personal communication, 2002.

Patents

Patents, including those filed in the U.S., contain reasonable speculation on the scope of a

reaction beyond their working examples. Use only subject matter from an actual working

example, preferably from the U.S. equivalent of a foreign patent. Examples:

Mathias, L. J.; Kosefoglu, S. H. U.S. Patent 4,889,948 (1989).

Nukui, K.; Kamya, K. Japanese Patent 05125050 (1993).

Wilkes, B.; Naumann, D.; Rudolph, W.; Sander, R. German Patent 3,623,184 (1988).

Allmendinger, T.; Differding, E.; Lang, R. W. European Patent 311,086 (1989).

Muller, G. W.; Stirling, D. I.; Chen, R. S.-C.; Man, H.-W. Intl. Patent WO 99/46258

(1999).

20

TABLES

• REFER TO APPENDIX III FOR THE CHEMDRAW SETTINGS USED FOR TABLE

PREPARATION, CONSTRUCTION OF SUB-TABLES, AND SAMPLE TABLE ENTRIES

FILES.

• Include all examples of the reaction that is being surveyed. The Editorial Board will

consider the possibility of publishing a less inclusive Tabular Survey under rare

circumstances. An exception could be considered, for example, if the Tables would

contain many listings of non-optimal reaction conditions for a transformation. If the

added value of certain table entries is in question, discuss the option of less inclusive

Tables with the Responsible Editor for the chapter. Written approval of the Editor-In-

Chief will be required ultimately for exercise of this option.

• If Charts are used at the beginning of the Tabular Survey to depict structures of ligands,

catalysts, or other reagents that are indicated by bold numbers in the tables, make

reference to these Charts in the introduction to the Tabular Survey, and also on the first

page of every new Table (e.g, on the first pages of Tables 1, 2, …etc.).

• Table entries are to be organized by substrate, and ordered by carbon-count of the

substrate. In rare cases, where such organization of the Tabular Survey is not desirable,

the author must have approval from the Responsible Editor and the Editor-In-Chief for an

alternative organization.

• Adhere to the format described in detail below, using ChemDraw software. (See

“Preparation of the Chapter,” page 3).

• Do not prepare Table pages using a mixed format, e.g. ChemDraw/Microsoft Word. All

Table pages must be ChemDraw documents.

• Do not use the multi-page (poster) feature of ChemDraw. Each ChemDraw file must be a

single page.

• Submit at least ten sample table pages as ChemDraw files (together with text graphics

and manuscript samples) to the Responsible Editor after the chapter outline has been

approved. Tight style requirements make it imperative that authors supply sample table

entries at the earliest possible time in chapter preparation.

• Obtain written approval from the Responsible Editor before deviating from the standard

format.

All authors are given a recent volume of Organic Reactions as further guidance in setting

up their Tabular Survey, and they are urged to examine the Tables in this volume and raise any

questions about format with the Responsible Editor or Editorial Coordinator. Authors must not,

however, try to duplicate the size or two-page layout of the final printed copy, as this

21

presentation is accomplished by the compositor from the supplied ChemDraw documents

containing the table entries.

Authors must become familiar with the instructions given in the following section, and

direct any questions to their Responsible Editor and the Editorial Coordinator.

Table Format

General Instructions

Authors are referred to the “For Authors” link on the Organic Reactions on Wiley Interscience

web site for a Power Point tutorial on table preparation: http://www3.interscience.wiley.com/cgi-

bin/mrwhome/107610747/ForAuthors.html.

• DO NOT USE THE MULTI-PAGE FEATURE (“POSTER”) IN CHEMDRAW VERSION

8.0 OR HIGHER. Each page of table entries must be a separate ChemDraw file. The

“poster” feature is not designed to accommodate multiple pages as are required in

Organic Reactions’ chapters.

• Create a stationery file for each Table using the OR Table Stationery 2012.cds file

provided by the Editorial Coordinator as a template. Give each Table a number and a

title. Number Tables using Arabic numerals. The first letter of each word in the title is in

12-pt (except for prepositions and conjunctions), and the remaining letters in 10-pt, all

CAPS. Subdivisions, if used, should be numbered 2A, 2B, etc. The column headers may

remain the same as in the generic stationery file, but the substrate column should be more

descriptive if possible, e.g., amine, keto ester, etc. Center the column headings. Adjust

column widths to best suit the anticipated entries, but leave both the guide-marks on the

ends and the reference column guide-mark fixed. Once column widths are set, they must

remain constant throughout a given Table.

• Select “Save as…” from the file menu to save the file as a new stationery file (.cds not

.cdx). Once this new stationery file is opened it will become the default new document.

Use this stationery file for every page of entries in that particular Table for which it was

designed. Create a new stationery file with an appropriate header when beginning each

new Table.

• Construct and label table entries. Open a new stationery file as created above. Draw

structures and type conditions and references for each table entry. (The proper drawing,

atom label, and caption settings are part of the document settings in OR Table Stationery

2012.cds, and will be in any new stationery file created from using this file as a template

unless actively changed. These settings are shown in Appendix III.) When a structure

contains more than one object, e.g., brackets, parentheses, stereochemical notations,

footnote letters, etc., group them together using “Group” in the “Object” menu. This step

22

will ensure that the structure stays intact during subsequent alignment procedures.

Otherwise, do not group entries.

• Include only 3 or 4 entries per page, and separate them with a dotted line. (Leave extra

space on the page in case insertion of an additional entry may be necessary later.) Label

each entry as to its Table and order in which it is to appear. For example, Tab01e004

indicates that the entry should be the fourth one in Table 1. Make every effort to have the

order as close as possible to the final order.

• After all the entries are made, align the contents of each column using the “left edges”

alignment tool in the “Object” pull down menu. The contents of each column are left-

aligned with the left-most guide-mark of that column. Then align each entry using “T/B

centers”. Use 16-pt line spacing in all text boxes. See Appendix III for sample files.

• Arrange entries within each Table in order of increasing carbon number of the

starting material. The carbon count should be based on all the carbon atoms that define

the substrate minus carbons in standard protecting groups not involved in the reaction.

Simple alkyl and aryl groups on oxygen and nitrogen should also be eliminated from the

count if it allows for the grouping of reactions that together demonstrate the effects of

simple structural variations on the outcome of a reaction. Use C5, C6, etc. next to the left-

hand margin (use left-most header guide-mark) of the page slightly above the entry. If a

set of similar substrates is grouped in one entry by using a sub-table, show the count as a

range, for example C5–11. Put such an entry in the carbon count group of the lower end of

the range, in this example the C5 group.

• Repeat carbon counts, starting materials, and products for each entry.

• Name the file. Name each file so that it is identifiable by author, table number, and

insertion numbers: DenTab01e121–124 denotes that this file has entries 121–124 for

Table 1 in the Denmark chapter.

• To insert additional entries at a later time, either insert it into the proper file, or, if it will

not fit, simply create a new page for the additional entry, and name it alphanumerically.

An insertion code of Tab01e004a would put the entry between Tab01e004 and

Tab01e005. (See sample files in Appendix III.)

23

Table Columns

Carbon Count

• Every entry must have the carbon count shown as described above.

Substrate/Starting Material

• Repeat the structure for the starting material in each entry.

Conditions

• Use the general text conventions given on page 8 for captions in the tables, except where

noted.

• Capitalize the first word of a Conditions entry (except rt).

• Give reactant (if not in a separate column), catalyst, solvent, temperature, and time, in

that order. Use “rt” for room temperature, and “eq” for equivalents.

• If it is necessary to use a structure in the Conditions column, apply 85% scaling, keeping

the atom labels as 10-pt font size. (Do not scale atom labels.)

• Do not include molar and volume ratios, or isolation procedures, unless they are critical.

• Repeat the conditions for each entry.

• Use the em-dash (option-shift-hyphen on a Macintosh) if conditions are not reported.

• Do not include equilibrium constants or other thermodynamic data in Tables.

• Use an en-dash for minus signs, and for number ranges (e.g., temp, time, yields).

• If the entry requires more than one print line, the 2nd and succeeding lines should be

indented by 2 spaces. If the entry involves sequential steps, number them 1., 2., [NOT 1),

2)], and do not indent succeeding lines. Use 16-pt line spacing.

Product(s) and Yield(s) (%)

• Enter the structures of the products. If there is not space for multiple products, use 2nd,

3rd, etc. lines, indenting a few spaces from the initial product(s). If more than one large

product structure is needed, draw partial structures for them, using a bracket, { or }, to

indicate the missing portion.

• Write yields in parentheses without the % sign [e.g., (80)] and enter them following each

product. Do not enter yields in a separate vertical column unless they are part of a sub-

table within an entry. Use the symbol (—) (shift-option-hyphen on the Macintosh) when

no yields are reported.

NH3/Li, THF,

aniline, –50°, 5 h

1. THF, –78°

2. Me3SiCl, Et3N,

HMPA, –78° to rt

24

• Do not set ratios of products and isomers in parentheses.

• Whenever possible, use “er” instead of “ee”, and specify absolute configuration.

• Use Roman numerals to show combined yield and product ratios for two or more

products. Do not continue the Roman numeric sequence beyond one set of entries, but

restart at I for each new series. The plus sign and slash are plain type, not boldface.

References

• Use temporary reference codes for table entries, as described earlier in this Guide.

• Each entry must have a reference. If there is more than one reference for an entry, the

first reference should be the one on which the entry is based, regardless of numerical

order.

• When a sub-table is constructed from the same reference, use the reference number once

in alignment with the structures. If different references contribute to the sub-table, show

each reference in the reference column in line with the corresponding sub-table entry.

Sub-Tables

• Because the content of Organic Reactions is ultimately entered into an online structure-

searchable database, the use of sub-tables in individual table entries should be limited to

those examples where the substrates and/or products are simple analogs, or where the

substrate and product(s) remain the same and conditions differ only slightly (e.g., same

reagents, but different catalysts, times, or temperatures). The use of sub-tables is

recommended for analysis of the effects of simple structural changes or alteration of

conditions on the outcome of a reaction, if arrangement by carbon count separates the

related entries. Arrange sub-tables by increasing carbon count. Substituents are always

drawn with attachment points on the right except for hydrocarbon substituents (including

CHO), which are drawn in the direct form; use an en-dash after potentially ambiguous R

groups such as cyano and isocyano (NC–, CN–). Complete instructions for constructing

sub-tables are given in Appendix III, page 38.

NO2 NO2

Ph

+

I III + II (84), I/II = 99:1

25

Example 1: Orientations of R and Ar Abbreviations in Sub-Tables.

Example 2: Entry Having Different Conditions (references not shown).

Example 3: Entry Where Substrates/Products are Simple Analogs, and Conditions Differ

(references not shown).

H2N

O2N

NC–

CN–

MeO

BnO

Ph

Py

1-Np

3-MeC6H4

3-MeOC6H4

2,5-(MeO)2C6H3

MeO2S

CF3CO

AcO

AcOCH2

EtO2C

4-TolSO3

Me

CF3

CHO

t-Bu

n-C5H11

c-C6H11

C8

n-BuTeBF3– K+

Pd(PPh3)4 (20%), base (2 eq),

additive (2 eq),

MeOH, ultrasound, 20 min

PhPh

Ph Ph

Base

K2CO3

Cs2CO3

Et3N

Et3N

Additive

Ag2O

Ag2O

Ag2O

AgOAc

(65)

(67)

(66)

(84)

NN

S SR2

R1

R1

R2

See table

C10–12

R1

H

Me

Me

R2

H

H

Me

Solvent

benzene

benzene

octane

Temp (°)

40

reflux

130

Time (h)

15

2

1

(60)

(100)

(85)

26

Footnotes

• Use italicized, lower case, superscript letters at pertinent parts of the Table for footnotes.

Collect footnotes into a dedicated file for that particular Table. Write footnotes as

complete sentences. The alphabetical sequence for footnotes begins anew in each Table

or Table subdivision. Thus, there will be a page for footnotes from Table 1, beginning

with “a”, and a separate page for footnotes for Table 2, also beginning with “a”, and so

forth.

• Authors are encouraged to keep, and submit, a separate list of the locations (table and

entry number) of all table footnotes to make it easier to find them in case later additions

require a change in their sequence. Such a list would be easy to compile while

constructing the tables, and would help reviewers in determining that all footnotes are in

place and in the correct sequence.

EDITING THE MANUSCRIPT

AUTHORS ARE REQUIRED TO PROVIDE THEIR RESPONSIBLE EDITOR WITH A

DETAILED CHAPTER OUTLINE, AND, ONCE THE OUTLINE IS APPROVED, SAMPLES OF

TEXT, TEXT GRAPHICS, AND TABLES AT THE BEGINNING OF THE CHAPTER

PREPARATION PROCESS. Departures from Organic Reactions style and format must be

detected early to avoid unnecessary expenditure of the authors’ and Organic Reactions' time and

effort in making revisions.

Authors will have an opportunity to review page proofs of their chapter. In order that

corrections are not misinterpreted, authors should use conventional copy editing and

proofreading symbols (Appendix VI).

27

APPENDIX I: Equation Files and Insertion Numbers

The following two pages illustrate (1) a ChemDraw file containing text equations that are

to be inserted into the text by the compositor; and (2) a sample text page illustrating how the

submitted version is to look with the insertion numbers and equations.

28

APPENDIX I (continued)

Sample ChemDraw Equations File Showing Insertion Numbers (top left corner)

1

R2

R1

R3

OH R2

R1

R3

OYM•

– MYO

MH

– M•R2

R1

R3

H (Eq. 1)

2

H

R1

R2

OY

S

H

R1

R2

H

3

O

O

OH

O

OMeSC(S)O

Bu3SnH, toluene

reflux, 18 h

O

O

OH

O

O(84%) (Eq. 2)

(Eq. 3)

4

5

(Eq. 4)

H

R1

R2

OY

SSnBu3

OY

SSnBu3

+Bu3SnH

Scheme 1

Bu3Sn•

O

OS

OH

Bu3SnH

OC(S)Y

OC(S)Y Bu3SnH

Bu3Sn•

•

R1

R2 R3•

Y = SMe, Ph,

imidazol-1-yl

R1

R2 H•

29

APPENDIX I (continued)

Sample Text with Equation Insertion Numbers

A high-yielding way to realize this sequence was first described by Barton and

McCombie{Barton, 1975 #1489} using the free-radical chain reaction of O-thioacyl derivatives

of secondary alcohols with tri-n-butylstannane (Bu3SnH), as shown in Scheme 1.

(2)

A typical deoxygenation of an O-(methylthiothiocarbonyl) derivative (an S-methyl

xanthate) of a secondary alcohol is shown in Eq. 2.{Barton, 1975 #1489}

(3)

Since the initial discovery, variations in the nature of the thiocarbonyl substituent (Y) and

the propagating radical/H-donor combination have provided options for fine-tuning both the

derivatization and reduction steps.

H

R1

R2

OY

S

H

R1

R2

HH

R1

R2

OY

SSnBu3

OY

SSnBu3

+Bu3SnH

Scheme 1

Bu3Sn•

Bu3Sn•

•

Y = SMe, Ph,

imidazol-1-yl

R1

R2 H•

O

O

OH

O

OMeSC(S)O

Bu3SnH, toluene

reflux, 18 h

O

O

OH

O

O(84%) (Eq. 2)

30

APPENDIX II: Guidelines for Computer-Drawn Text Graphics

The ChemDraw files for the text graphics must be submitted with the manuscript. Points of

insertion for the graphics should be noted in the text just above the graphic itself (see Appendix

I).

A ChemDraw stationery file (OR TxGr Stationery 2012.cds) with the following settings is

provided via e-mail. This file should be used as the style template for drawing text graphics.

Text graphics should be constructed with the page setup as “US Letter” in "portrait" mode.

The following settings for text graphics are shown in ChemBioDraw Ultra 11.0 document

settings windows, but are also applicable to earlier and later versions.

31

32

33

APPENDIX II (continued)

Annotated Example of Text Equation

* * * * * * * * *

When processed by our publisher, the equation printed in the actual volume at 67%

reduction will look like this:

OO

YO

Y = Si(t-Bu)2

R = PMBO(CH2)3

H

HMeSC(S)O

RCO2Bu3SnH, AIBN

benzene, refluxO

O

YO

H

HRCO2

OO

YO

H

HRCO2

+ (Eq. 44)

[M]

0.125

0.003

[M] = initial substrate molarity

42 43

42 + 43

90

50

42:43

>95:5

<5:95

si

Yield (%)

Text settings (all)

font = Times or Times Roman

size = 12 pt

line spacing = 16 pt

bond length = 16.2 pt

line width = 0.5 pt

bond spacing = 2.92 pt

hash spacing = 2.5 pt

a For two-line conditions, use a single text box with 20-pt line spacing and center it over the arrow.b If there is room, center the Eq. # on the line of the arrow. If not, place it below and to the right

within the width guidelines.

Preferred maximum 7" (17.8 cm)

Absolute maximum 7.25" (18.4 cm)

medium-head arrow

a

b

OO

YO

Y = Si(t-Bu)2

R = PMBO(CH2)3

H

HMeSC(S)O

RCO2Bu3SnH, AIBN

benzene, refluxO

O

YO

H

HRCO2

OO

YO

H

HRCO2

+ (Eq. 44)

[M]

0.125

0.003

[M] = initial substrate molarity

42 43

42 + 43

90

50

42:43

>95:5

<5:95

si

Yield (%)

34

APPENDIX III: Guidelines for Computer-Drawn Tables

[Authors are referred to the “For Authors” link on the Organic Reactions on Wiley

Interscience web site for a Power Point tutorial on table preparation:

http://www3.interscience.wiley.com/cgi-bin/mrwhome/107610747/ForAuthors.html]

A ChemDraw stationery file (OR Table Stationery 2012.cds) with the following settings is

provided via e-mail. This file should be used as the style template for drawing table entries.

The following settings for table entries are shown in ChemBioDraw Ultra 11.0 document

settings windows, but are also applicable to earlier versions. Tables are prepared using US Letter

size pages in landscape orientation. Note that “Pages” NOT “Poster” is selected in the Layout

tab. The multi-page feature is NOT an option for the preparation of Organic Reactions Tables.

While the "Drawing" settings are the same as those required for text graphics, the

"Captions" and "Atom Labels" settings differ. Use 10-pt Times in both the "Captions" and "Atom

Labels" settings; use fixed 16-pt line-spacing for captions, and fixed 9-pt line-spacing for atom

labels.

35

36

37

38

APPENDIX III (continued)

Construction of Sub-Tables

As discussed and illustrated on page 24, sub-tables should be limited to those examples

where the substrates and/or products are simple analogs, or where the substrate and product(s)

remain the same but conditions differ. Create one column, including the header, at a time. Do not

put multiple columns in a single text box. Text should be left-justified. Numerical data such as

yields, temperature, and time should be centered. All line spacing should be 16-pt.

Type the header first and then add the data. After the first column is complete, select it, and

while holding the option and shift keys (Macintosh), or the shift and control keys (Windows),

drag a copy to the right. This is now the second column of the sub-table, which can be

overwritten with the next set of information. Continue this process to complete the sub-table, add

a line (from the brackets icon in the drawing tools) under the column headings, then group

(“Objects” menu). Put yields in parentheses in the last column. If there are different references in

a sub-table, enter them in the reference column in the same rows as the entries to which they

refer.

Scale partial structures in sub-tables by 85%, keeping the atom labels in 10-pt font size.

Sample Table Files

The following two pages show how a finished page of table entries should appear. The first

page shows a set of table entries, and the second shows the same set of entries plus an insertion,

should adding an entry be necessary.

Ar1

4-FC6H4

4-ClC6H4

4-MeOC6H4

4-NCC6H4

4-O2NC6H4

4-MeO2CC6H4

3,4-(MeO)2C6H3

Ar2

Ph

4-ClC6H4

Ph

4-NCC6H4

4-MeO2CC6H4

4-MeC6H4

4-MeC6H4

R1

MeO2C

MeO2S

MeO2S

MeO2S

R2

Me

Me

Ph

Ph

Temp (°)

80

35

101

101

Time (h)

1

3

24

24

(64)

(66)

(29)

(43)

R1

TMS

Me

I + II

(89)

(96)

(82)

I/II

4.2:1

2.7:1

6.3:1Si

Me

Me

39

Alcohol Refs.Conditions Product(s) and Yield(s) (%)

TABLE 1. OXIDATIONS OF MONOFUNCTIONAL ALCOHOLS (Continued)

[HO-TEMP=O]+Br–, MeOH, reflux (97)a {Chmielewska, 1995 #953}O

HC2

OH

Tab01e004

C3

{Chmielewska, 1995 #953}HO-TEMPO (cat.), electrolysis,

Na2SO4, H2O, acetate buffer, pH 4–5, rt

OH (—)

O

H

Tab01e005

O

C3



OH (—)

Tab01e006

OH

C4

HO-TEMPO (cat.), electrolysis,


{Chmielewska, 1995 #953}(—)

Tab01e007

Filename has the form AuthTab01-e004-007

Sample File 1

Notation indicates that this record is the

4th entry in Table 1.

H

O

These column widths may be adjusted as necessary, but must

remain constant throughout a given Table, e.g., Table 1.

40

Alcohol Refs.Conditions Product(s) and Yield(s) (%)

TABLE 1. OXIDATIONS OF MONOFUNCTIONAL ALCOHOLS (Continued)

[HO-TEMP=O]+Br–, MeOH, reflux (97)a {Chmielewska, 1995 #953}O

HC2

OH

Tab01e004

C3



OH (—)

O

H

Tab01e005

OH

C4

HO-TEMPO (cat.), electrolysis,


{Chmielewska, 1995 #953}(—)

Tab01e007

Tab01e006-eliminated

Tab01e004a

O

C3



OH (—)

This file is a revision of the previous page, illustrating how to handle insertion/deletion.

Filename has the form AuthTab01-e004-007

Sample File 2

H

O

41

APPENDIX IV: Use of EndNote! for Tracking Table References

EndNote! is a powerful tool for organizing references in a Word document but

cannot be used in ChemDraw. However, it can be used quite successfully to track and

organize Table references and generate them in the proper order for the final manuscript.

The following outlines a procedure, and examples follow. Note that the examples are for

illustrative purposes only and do not suggest where reference numbers should begin. Also

the references generated from EndNote after the manuscript is completed should appear

at the end (as endnotes), not in the body (as footnotes) of the text.

• Enter all the chapter references, including those used for Table entries, in a

designated EndNote Library.

• Using a list of the reference library printed from EndNote (or other existing

reference catalog such as index cards), manually assign temporary codes (see

suggested method in “References” section beginning on page 16 of this

Manuscript Guide) to all the references and use these temporary codes throughout

the Tables. Be sure to retain, for your reference, an electronic copy of the Tables

with the temporary codes should rearrangement of entries be requested later.

• As you compile each Table, list the reference codes in a Word document,

identifying them by Table section and page number to facilitate making

corrections later (A).

• Using the EndNote Library, assign a reference citation to each of the codes in the

Word document (B). Be sure to keep the temporary codes adjacent to their

corresponding citations.

• If, during the course of preparing the Manuscript, the order of the references on

any page in the Tables should change, rearrange or edit the Table reference list

accordingly.

• Once the manuscript is in the form for final submission, insert the Table reference

list at the end of the chapter manuscript, creating a single Word document. These

pages can easily be removed later.

• At this point, consult with the Responsible Editor for the chapter and determine

whether or not he/she would prefer the document as is, with citations (include

electronic and hard copies of the EndNote Library), or with the reference numbers

generated via completing the EndNote process (C).

• In any case, submit the chapter with the temporary codes still in the Tables.

42

APPENDIX IV (continued)

A: Table 1, page 001

(codes as they appear in the Tables)

AMG96

BLP89

SSP89

KKL87

BEM94

page 002

BSB93

MWR98

DP99 B: Table 1, page 001

(MS Word document listing)

AMG96 [Alazard, 1996 #1801]

BLP89 [Boschi, 1989 #1044]

SSP89 [Seebach, 1989 #486]

KKL87 [Knors, 1987 #1194]

BEM94 [Brown, 1994 #934]

page 002

BSB93 [Brunner, 1993 #2018]

MWR98 [Moyesherman, 1998

#2358]

DP99 [Davies, 1999 #2536]

C: Table 1, page 001

(References after EndNote conversion. Do

NOT do this step unless asked to do so by

the Editorial Coordinator.)

AMG96165

BLP89166

SSP89167

KKL87168

BEM94169

page 002

BSB93170

MWR98171

DP99172

This is how the references will appear at the end of the document: 165. Alazard, J.-P.; Millet-Paillusson, C.; Guenard, D.; Thal, C. Bull. Soc. Chim. Fr. 1996, 133,

251.

166. Boschi, T.; Licoccia, S.; Paolesse, R.; Tagliatesta, P.; Pelizzi, G.; Vitali, F. Organometallics

1989, 8, 330.

167. Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377.

168. Knors, C.; Kuo, G. H.; Lauher, J. W.; Eigenbrot, C.; Helquist, P. Organometallics 1987, 6,

988.

169. Brown, D. S.; Elliott, M. C.; Moody, C. J.; Mowlem, T. J.; Marino, J. P., Jr.; Padwa, A. J.

Org. Chem. 1994, 59, 2447.

170. Brunner, H.; Singh, U. P.; Boeck, T.; Altmann, S.; Scheck, T.; Wrackmeyer, B. J.

Organometal. Chem. 1993, 443, C16.

171. Moyesherman, D.; Welch, M. B.; Reibenspies, J.; Burgess, K. Chem. Commun. 1998, 2377.

172. Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett. 1999, 40, 5287.

43

APPENDIX V: The Journal of Organic Chemistry Standard Abbreviations and Acronyms

Available as a pdf file from the Journal of Organic Chemistry: http://pubs.acs.org/userimages/ContentEditor/1218717864819/joceah_abbreviations.pdf

! observed optical rotation in degrees

[!] specific rotation [expressed without units; the units, (deg⋅mL)/(g⋅dm), are understood]

Å angstrom(s) Ac acetyl acac acetylacetonate ADP adenosine 5"-diphosphate AIBN 2,2"-azobisisobutyronitrile AM1 Austin model 1 AMP adenosine 5"-monophosphate Anal. combustion elemental analysis anhyd anhydrous AO atomic orbital aq aqueous Ar aryl atm atmosphere(s) ATP adenosine 5"-triphosphate ATPase adenosinetriphosphatase av average 9-BBN 9-borabicyclo[3.3.1]nonyl 9-BBN–H 9-borabicyclo[3.3.1]nonane Bn, Bzl benzyl bpy 2,2"-bipyridyl BOC, Boc tert-butoxycarbonyl bp boiling point, base pair br broad (spectral) Bu, n-Bu normal (primary) butyl s-Bu sec-butyl t-Bu tert-butyl Bz benzoyl (not benzyl) B3LYP 3-parameter hybrid Becke

exchange/Lee–Yang–Parr correlation functional

°C degrees Celsius calcd calculated cAMP adenosine cyclic 3",5"-phosphate CAN ceric ammonium nitrate CASSCF complete active space self-

consistent field CASPT2 complete active space with

second-order perturbation theory

cat catalytic CBZ, Cbz benzyloxycarbonyl (preferred

over the abbreviation Z) CC coupled cluster

CD circular dichroism cDNA complementary deoxyribonucleic

acid c-Hex, c-C6H11 cyclohexyl CI chemical ionization;

configuration interaction CIDNP chemically induced dynamic

nuclear polarization cm centimeter(s) cm–1 wavenumber(s) cod 1,5-cyclooctadiene compd compound concd concentrated concn concentration COSY correlation spectroscopy cot 1,3,5,7-cyclooctatetraene Cp cyclopentadienyl m-CPBA meta-chloroperoxybenzoic acid CV cyclic voltammetry # chemical shift in parts per

million downfield from tetramethylsilane d day(s); doublet (spectral); deci d density DABCO 1,4-diazabicyclo[2.2.2]octane dansyl 5-(dimethylamino)-1-

naphthalenesulfonyl DBN 1,5-diazabicyclo[4.3.0]non-5-ene DBU 1,8-diazabicyclo[5.4.0]undec-7-

ene DCC N,N"-dicyclohexylcarbodiimide DCE 1,2-dichloroethane DDQ 2,3-dichloro-5,6-dicyano-1,4-

benzoquinone DEAD diethyl azodicarboxylate DEPT distortionless enhancement by

polarization transfer DFT density functional theory DIBALH diisobutylaluminum hydride DMA dimethylacetamide DMAP 4-(N,N-dimethylamino)pyridine DMDO dimethyldioxirane DME 1,2-dimethoxyethane DMF dimethylformamide DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-

2(1H)-pyrimidinone DMSO dimethyl sulfoxide DMTrCl 4,4"-dimethoxytrityl chloride DNA deoxyribonucleic acid DPS tert-butyldiphenylsilyl

44

dr diastereomeric ratio DTT dithiothreitol E1 unimolecular elimination E2 bimolecular elimination

ED50 dose that is effective in 50% of test subjects

EDTA ethylenediaminetetraacetic acid EI electron impact EPR electron paramagnetic resonance eq equation equiv equivalent

er enantiomeric ratio ESI electrospray ionization Et ethyl FAB fast atom bombardment FD field desorption FID flame ionization detector; free induction decay

Fmoc 9-fluorenylmethoxycarbonyl FT Fourier transform g gram(s); prefix to NMR

abbreviation denoting gradient-selected (e.g. gCOSY, gHMQC)

GC gas chromatography

GTP guanosine 5!-triphosphate h hour(s) HF Hartree–Fock HMBC heteronuclear multiple bond

correlation HMPA hexamethylphosphoric triamide

(hexamethylphosphoramide)

HMQC heteronuclear multiple quantum correlation

HOMO highest occupied molecular orbital

HPLC high-performance liquid chromatography

HRMS high-resolution mass

spectrometry HSQC heteronuclear single quantum

correlation Hz hertz ICR ion cyclotron resonance INDO intermediate neglect of

differential overlap

IP ionization potential IR infrared J coupling constant (in NMR

spectrometry) k kilo K kelvin(s) (absolute temperature) L liter(s)

LAH lithium aluminum hydride LCAO linear combination of atomic

orbitals LD50 dose that is lethal in 50% of test

subjects

LDA lithium diisopropylamide; local density approximation

LFER linear free energy relationship LHMDS lithium hexamethyldisilazane,

lithium bis(trimethylsilyl)amide

lit. literature value (abbreviation used with period)

LTMP lithium 2,2,6,6-tetramethylpiperidide

LUMO lowest unoccupied molecular

orbital µ micro m multiplet (spectral); meter(s);

milli M molar (moles per liter); mega M

+ parent molecular ion

MALDI matrix-assisted laser desorption

ionization max maximum MCD magnetic circular dichroism MCR multicomponent reaction MCSCF multi-configuration self-

consistent field MD molecular dynamics

Me methyl MEM (2-methoxyethoxy)methyl Mes 2,4,6-trimethylphenyl (mesityl)

[not methylsulfonyl = mesyl] MHz megahertz min minute(s); minimum mM millimolar (millimoles per liter)

MO molecular orbital mol mole(s); molecular (as in mol wt) MOM methoxymethyl mp melting point MP Møller–Plesset perturbation

theory MRCI multi-reference configuration

interaction mRNA messenger ribonucleic acid Ms methylsulfonyl (mesyl) MS mass spectrometry MTBE methyl tert-butyl ether MW, mol wt molecular weight m/z mass-to-charge ratio (not m/e)

N normal (equivalents per liter) NAD

+ nicotinamide adenine

dinucleotide NADH reduced NAD NBO natural bond orbital NBS N-bromosuccinimide NCS N-chlorosuccinimide

NICS nucleus-independent chemical shift

nm nanometer(s) NMO N-methylmorpholine-N-oxide NMP N-methylpyrrolidone

45

NMR nuclear magnetic resonance NOE nuclear Overhauser effect NOESY nuclear Overhauser effect

spectroscopy

NRT natural resonance theory Nu nucleophile obsd observed OD optical density ORD optical rotary dispersion PCC pyridinium chlorochromate PDC pyridinium dichromate

PES photoelectron spectroscopy Ph phenyl piv pivaloyl pm picometer(s) PM3 parametric method 3 PMB p-methoxybenzyl PPA poly(phosphoric acid)

ppm part(s) per million PPTS pyridinium para-

toluenesulfonate Pr propyl i-Pr isopropyl PT perturbation theory PTC phase-transfer catalysis

py pyridine q quartet (spectral) QSAR quantitative structure–activity

relationship RCM ring-closure metathesis redox reduction–oxidation rel relative

Rf retention factor (in chromatography)

RHF restricted Hartree–Fock ROESY rotating frame Overhauser effect

spectroscopy ROMP ring-opening metathesis

polymerization

rRNA ribosomal ribonucleic acid rt room temperature s singlet (spectral); second(s) SAR structure–activity relationship SCF self-consistent field SEM scanning electron microscopy SET single electron transfer

SN1 unimolecular nucleophilic substitution

SN2 bimolecular nucleophilic substitution

SN! nucleophilic substitution with allylic rearrangement

SOMO single-occupied molecular orbital

t triplet (spectral) t time; temperature in units of

degrees Celsius (ºC) T absolute temperature in units of

kelvins (K)

TBAB tetrabutylammonium bromide TBAC tetrabutylammonium chloride TBAF tetrabutylammonium fluoride TBS tert-butyldimethylsilyl

TBHP tert-butyl hydroperoxide TCA trichloroacetic acid TCNE tetracyanoethylene TDDFT time-dependent density

functional theory TEAB tetraethylammonium bromide temp temperature

Tf trifluoromethanesulfonyl (triflyl) TFA trifluoroacetic acid TFAA trifluoroacetic anhydride THF tetrahydrofuran THP tetrahydropyran-2-yl TIPS triisopropylsilyl TLC thin-layer chromatography

TMAI tetramethylammonium iodide TMEDA N,N,N!,N!-tetramethyl-1,2-

ethylenediamine TMS trimethylsilyl; tetramethylsilane TOF time-of-flight Tr triphenylmethyl (trityl) tRNA transfer ribonucleic acid tR retention time (in

chromatography) Ts para-toluenesulfonyl (tosyl) TS transition state UHF unrestricted Hartree–Fock UV ultraviolet VCD vibrational circular dichroism

vis visible vol volume v/v volume per unit volume (volume-

to-volume ratio) wt weight w/w weight per unit weight (weight-

to-weight ratio)

ZINDO Zerner parameterization of intermediate neglect of differential overlap

46

APPENDIX VI: Copy Editing and Proofreading Symbols

Documents

October 2011 - Organic Reactions Wikiorganicreactions.org/images/a/af/ManuscriptGuide_2012.pdfORGANIC REACTIONS MANUSCRIPT GUIDE Overview This document provides guidelines for the