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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



This edition first published 2008

2008

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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

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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.

技

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:



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



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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