Organic synthesis the disconnection approach 2nd edition by stuart warren (1)

Bạn đang xem bản rút gọn của tài liệu. Xem và tải ngay bản đầy đủ của tài liệu tại đây (7.38 MB, 340 trang )

Organic Synth臼is;
The Disconnection Approach
2日d Edition

vn

Stuart 飞毛Tarre室主

and

m
4a
ll.

u瓦

Department,

he

Paul Wyatt

of Bristol ,

ht

tp

://

w

w

w

.c

Schoolof

⑧WIL盯
AJohn 飞iVìley and Sons, Ltd" Publication

U瓦

This edition first published 2008
2008 John 飞的 ley & Sons , Inc.

Registered 01.声
& Sons

John 皆iley

Ltd， τhe

Chichester，有部 t Suss帜，

Atrium , Southem Gate.

P019

8S龟 United

Kingdom

For details of our global 时itorial offices , for customer services and for infonnation about how to apply for
permission to 陀use the copyri在ht material in this book please see our website at www.wiley.com.
τhe

right of the author to be identified as the author of this work has been asserted in accordance with the
Copyright , Desi 盯1S and Patents Act 1988.
A l\ rights reserved. N 0 P缸t of this publication 部ay be reproduced , stored in a retrieval system , or transmitted , in
by
any fom1 or by any means , electronic , mechanical , photocopying , recording or otherwise , exc巳pt as
the UK Copyright , Designs and Patents Act 1988 噎 without the prior permissíon of the publisher.
认Tiley

vn

also publishes its books in a variety of electronic formats. Some content that appears in print may not be
avaHable in electronic books.

m
4a
ll.

Designations used by companies to distinguish their products are often daimed as trademarks. AH brand names
and product names used in this book are trade 凶m时， service marks , trademarks or registered trademarks of
their respective owners The publìsher is not associated with any product or v念ndor mentioned in this book. 丁his
publicatìon is designed to
accurate and authoritative information in regard to the subject matter covered.

It is sold on the understanding that the publisher is not engaged in rendering professional services. If
advice or other expert 揣在 istance is require丛 the services of cornpetent professional should be sough t.
‘

ht

tp

://

w
w

w

.c

he

The publísher and the author make no representations or warranties with respect to the accuracy or cornpleteness
of the contents of this work and 呼机ifically disclai 凯 all warranties ,
without limitation any implied
warranties of 岳tness for a particular purpose. This work sold with the understanding that the pubhsher is not
services. τhe ad飞忧e and strategies contained herein rnay not be suitable for
engaged in rendering
every situation. In view of ongoing research , equiprnent modifications , changes in govemmental regulation笃， and
the constant fiow of information relating to the use of experimental reagents , equipment警 and devices , the reader
is u塔ed to review and evaluate the information provided in the packagεinsert or instructions for each chemical ,
piece of equipment , reagent , or device for , arno只 g 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 andJor a potential source of further informatìon does not mean that the author or the publisher
endorses the information the organization or Website may pro飞lide or recornmendations it may rnake. Furth时，
readers should be aware that Internet Websites listed in this work may have changed or disappeared betw四只
when this work was written and when it is re我d. No waπanty 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.
LibraηI

0/ Congress

C.αtaloging-in-Pl￥blication

Data

Warren哩 Stuart

G.
Organic synthesís : the disconnection approach I Stuart Warren and Paul
p. cm.
Includes biblíographical references and index.
ISBN 978-0-470-71237-5 (cloth)一-ISBN 978-0斗70-71236-8 (pbk. :
alk. paper)
1. O~mic
L 百yatt， PauL n. 在tle.
QD262.W2842008
547'.2-dc22

Wyatt.一一 2nd

ed.

2008033269
A catalogue record for this book is available from the British
ISl日-l' 978-0-470-7份 12375 (HIB)

τypeset

978-0-470平 12368

(P!B)

in 10/12 Times-Roman by Laserwords Private Li mited , Chennai , India
Printed and bound in Great Britain by CPI Antony Rowe, Chippenham, Wiltshire

&zt

的部

gLvr

ht

tp

://

w
w

w

.c

he

m
4a
ll.

vn

主

C

a

巨

Marria口，… 2007 ，

stc
LHa
,
se
ih
c(adi
t

飞在rho

7￥&'也

ac

拿雹霉 -A

first
Marrian

to

vn

m
4a
ll.

he

.c

w

w
w

://

tp

ht

Co吕立f盟ts

Preface

lX

General References

XI

Basic
and
Strategy 1: The Order of Events
One-Group C-X Dìsconnections
Strate 2: v II:
C-X DisconnectÎ ons
III: Reversal of Polarity ,

7730J5531
li23345867

vn

Synthesis of Aromatic

m
4a
ll.

2.
3.
4.
5.
6.
7.
8.

of

Arnìn已

he

生 Strategy IV: Protecting
10. One Group C C Disconnections 1: Alcohols
11. General St栩如前r A:
a Disconnection
12. Strate玄v V:

VII: 盯se

tp

ht
技itro

23. 在NφGroup Disconnections IV:
Compounds
24.
Disconnections V:
25.
26. Strategy XII: Reconnection
27. Two-Group C…C Disconn巳ctions VI:
28. General
B: Strategy of Car七onyl Disconnections
29.
XIII: Introduction to
Synthesis: Saturated
30. Three品lernbered
XIV:
3 1.

'1

X:

豆

22.

://

(Alkynes)
of
C…C Disconnections 1: Diels-Ald时 Reactions

Strate 2: v VIII: Introduction to
在isconnections II:
Compounds
IX: Control in Car柱。nvl Condensations
C-C Disconnections III:
Compounds
Conjugate (Michael) Addîtion and Robinson Annelation

17.τwo-Group

18.
19.
20.
21.

w
w

15. Alkene
16. Strategy

212i$1·EAli2·

w

.c

…

151

161
167
177
185
193
199
207
217
229
237
245

Contents

VH呈

33.
XV:τhe Use of Ketenes in
34. Five-Mem如 ered
35. Strate Q. v XV I:

251
255
Special Methods
2岳 1

36.
37.
38.

39.
40.

Six-Membered Rings
General Strategy C:
XVII:
AromatÍC
D:A母 vanced
General

269
279
289
301
313

Synthesis

Index

ht

tp

://

w
w

w

.c

he

m
4a
ll.

vn

325

Preface
publìshed Organic
1于ze Disconnection Approach 色y Stuart
to the learning of synthesis has become
while the book Ìtself
is now dated in content and appearance ‘ In
唱Tiley published Organic
and Control by Paul Wyatt and Stuart 轧Tarren. Thís muc如柱。ok ís
as a
fourth year und巳 rgradu时es and research workers in universities and industry. The
workbook was published ìn 2008.τ如is new book made thεold one look very dated ín
and content and
gaps between what students were expectεd to understand in the 1980s
to understand now. This second edition is intended to fill some of
and what
are

those gaps.
The
of the
book is the same in the second edítion. It alternates chapters
new concepts wÌth strategy chapters that put 出e new work in the context of overall planning.
丁he 40 chapters have the same titles: some
have hardly been changed whíle others
have
a
revision with considerable amounts of new m剖erial. In most cases
from recent years are included.
in the pharmaceutical
One source of new material is the courses 出at the authors
Our 色asic course is 'The Disconnection Approach' and the 削aterial we have
for this
of the various compounds
course has reinforced our attempts to
reasons for the
for students. We
to
which we 忧 lieve enlivens the 加ok and makes it more
after the publication of the
a second edítíon of the workbook
The 民rst edition of th巳 textbook was in fact thεthird in a series of 品。oks on
by 乳
The firs t: The
an lntroduction to
如 1974 ， is a
book asking for a
of interaction with the reader who

was
to solve pro剖ems while
rarely use
now as the
method has 岳阳 n suplersedt~d 七 y interactive programmes on computers. Paul Wyatt is writín革 an
electronic book to replace The Cα rbonyl Group which will
a
of an electronic
七ook and 七ooks with associated workbooks in a uniform format that we hope will prove of
value as students of organic
develop their careers.

In the 26 years

since 有iley

ht

tp

://

w
w

w

.c

he