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Organic

S y n t h

臼 i s

The Disconnection pproach

日 d Edition

S t u a r t   a r r e

Department 

and

Paul Wyatt

choolof of Bristol  瓦

 

W L

 

J o h n ì l e y and Sons  Ltd Publication

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This edition first published 2008

2008

J o h n

飞 的   Sons  Inc.

Registered

J o h n

i l e y

 

Sons

τ h e

Atrium

 

Southem Gate.

C h i c h e s t e r

, 有 部

S u s s

帜 ,

P019

U n i t e d

Kingdom

For details of

our

g l o b a l

 

i t o r i a l offices

 

for customer services and for infonnation about how to apply for

permission to 陀 the c o p y r i material in this book please see our website at www.wiley.com.

τ h e right

of

the author to be identified as the author of this work has been asserted in accordance with the

Copyright   D e s i 盯 and Patents Act 1988.

Al\ rights reserved. N0 缸 of this p u b l i c a t i o n 部 be reproduced   stored in a retrieval system   or transmitted   in

any

fom1

or by any means   electronic   mechanical  photocopying   recording or otherwise  as by

the UK Copyright

 

Designs and Patents Act 1 9 8 8

w i t h o u t

the prior permissíon of the publisher

认 T i l e y also publishes its books in a variety of electronic formats. Some content that appears in print may not be

avaHable in electronic books.

Designations used by companies to distinguish their products are often daimed as trademarks. AH brand names

and product names used in this book are t r a d e   service marks

 

trademarks or registered trademarks of

their respective owners

‘ The

publìsher is not associated with any product

or

n d o r mentioned in this

b o o k . 丁

publicatìon is designed to accurate and authoritative information in regard to the subject matter covered.

It is sold on the understanding that the publisher

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not engaged in rendering professional services. If

advice or other

e x p e r t

揣 在

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The publísher and the author make no representations or warranties with respect to the accuracy or cornpleteness

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the contents of this work 呼 机 i f i c a l l y d i s c l a i

 

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for a particular purpose. This work sold with the understanding that the pubhsher is not

engaged in rendering services.

τ h e

飞 忧 and strategies contained herein rnay not be suitable for

every situation. In view

of

ongoing research  equiprnent modifications  changes in govemmental r e g u l a t i o n and

the constant fiow of information relating to the use of experimental reagents  e q u i p m e n t devices   the reader

is 塔 to review and evaluate the information provided in the

p a c k a g ε i n s e r t

or instructions for each chemical 

piece

of

equipment   reagent   or device for  a r n o 只 other things

any changes in the instructions or índication

of

usage and for added wamings and precautions. The fact that an organization or Website is referred to in this

work as a citation andJ

or

a potential source

of

further informatìon does not mean that the author or the publisher

endorses the information the organization or Website may

l i d e

or recornmendations it may rnake.

F u r t h

readers should be aware that Internet Websites listed in this work may have changed or disappeared b e t w

四 只

when this work was written and when it is No w a π a n t y may be created or extended by any promotional

statements for this work Neither the publisher nor the author shall be liable for any damages arising herefrom.

L i b r a 0

Congress

t a l o g i n g - i n - P l b l i c a t i o n

Data

W a r r e n

S t u a r t

G.

Organic synthesís : the disconnection approach I Stuart Warren and Paul

W y a t

t . 一 一 ed.

p. cm.

Includes biblíographical references and index.

ISBN 978-0-470-71237-5

c l o t h )

  I S B N 9 7 8 0

7 0 7 1 2 3 6 8 (pbk. :

alk. paper)

1 O ~ m i c 百 y a t t PauL 在 t l e .

QD262.W2842008

547 .2-dc22

A catalogue record for this book is available from the British

9 7 8 - 0 - 4 7 0 - 7 1 2 3 7 5

 HIB)

9 7 8 0 4 7 0

  1 2 3 6 8

(P

 B)

τ y p e s e t in 10 12 Times-Roman by Laserwords Private Limited  Chennai  India

2008033269

Printed and bound in Great Britain by CPI Antony Rowe  Chippenham  Wiltshire

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first

arrian

M a r r i a

  , 7

a

di

 a

s

h

 

L a

stc

 

zt

c

to

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  o

吕 立

f

t s

Preface

lX

General References

XI

2 Basic and

3

Strategy

:

The Order

of

Events

4. One-Group C X Dìsconnections

5 Strate   v II:

Synthesis of Aromatic

7730J553

li2334586

6.

7.

C X DisconnectÎons

III: Reversal of Polarity

 

of

8 A r n ì n

生 S t r a t e g y IV: Protecting

10 One Group C

C Disconnections

:

Alcohols

11 General 栩 如 A: a Disconnection

12 S t r a t e V:

Alkynes)

15.

Alkene

16.

Strategy

V I I :   of

1 7 . τ w o G r o u p C

C Disconnections : D i e l s A l d 时 R e a c t i o n s

18.

Strate

 

v VIII: Introduction to

i s c o n n e c t i o n s II:

IX: Control in Condensations

Compounds

9.

20.

21. C

-C

Disconnections III: Compounds

Conjugate Michael Addîtion and Robinson Annelation

22.

i t r o

φ r o u p Disconnections IV: Compounds

24.

25.

Disconnections V:

26.

Strategy XII: Reconnection

27.

Two-Group C

C D i s c o n n

c t i o n s

VI:

28.

General

B:

Strategy of o n y l Disconnections

29. XIII: Introduction to Synthesis: Saturated

30.

T h r e e  

l e r n b e r e d

151

161

167

177

185

193

199

207

217

229

237

245

31

XIV:

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33. X V τ h e Use of Ketenes n

34. F i v e M e m e r e d

35. Strate  v XV I

36. Six Membered Rings

37. General Strategy C:

38. XVII:

39. AromatÍC

40. General

D A v a n c e d

  ndex

ontents

Special Methods

Synthesis

251

255

269

279

289

301

3 3

325

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Preface

In the 26 years s i n c e 有 i l e y publìshed Organic Disconnection p p r o a c h Stuart

W a r r e n

, 由 自 a p p r o a c h

to the learning

of

synthesis has become while the book Ìtself

is now dated in content and a p p e a r a n c e 唱 T i l e y published Organic

and ontrol by Paul Wyatt and S t u a r t 轧 T a r r e n Thís m u 柱 ís as a

fourth year 巳 r g r a d u 时 and research workers in universities and industry. The

workbook was published ìn 2 0 0 8 τ new book made

t h ε o l d

one look very dated ín

and content and gaps between what students were

e x p e c t ε d to

understand in the 1980s

and what are

to

understand now. This second edition

is

intended

to

fill some

of

those gaps.

The of the book is the same in the second edítion.

t

alternates chapters

new concepts wÌth strategy chapters that put new work in the context

of

overall planning.

丁 40 chapters have the same titles: some have hardly been changed whíle others

have a revision with considerable amounts of new

e r i a

In most cases

from recent years are included.

One source of new material

is

the courses the authors in the pharmaceutical

a s i c course is The Disconnection Approach and 削 a t e r i a l we have for this

course has reinforced our attempts to reasons for the

of

the various compounds

which w

l i e v e

enlivens

 

and makes it more for students.

e

to

a second edítíon of the workbook after the publication of the

edition of t e x t b o o k was in fact t h ε t h i r d in a series on

 

firs t The an lntroduction t

如 1 9 7 4 is

a book asking for a of interaction with the reader who

was to solve 剖 while rarely use now as the

method 岳 阳 s u p l e r s e d t ~ d interactive programmes on computers. Paul Wyatt is w r i t í n

electronic book to replace The

r b o n y l

Group which will a

of

an electronic

o o k s

with associated workbooks in a uniform format that we hope will prove of

value as students of organic develop their careers.

Stuart a r r e n and aul 研

March 2008.

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