http:/

/www.ch

em4a

ll.vn

Organic Synth臼is;

The Disconnection Approach 2日d Edition

Stuart 飞毛Tarre室主Department, u瓦

and

Paul Wyatt Schoolof of Bristol, U瓦

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

http:/

/www.ch

em4a

ll.vn

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

Registered 01.声John 皆iley & Sons Ltd， τhe Atrium, Southem Gate. Chichester，有部t Suss帜， 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.

Al\ rights reserved. N 0 P缸t of this publication 部ay be reproduced , stored in a retrieval system, or transmitted, in any fom1 or by any means, electronic, mechanical , photocopying, recording or otherwise, exc巳pt as by the UK Copyright, Designs and Patents Act 1988噎 without the prior permissíon of the publisher.

认Tiley 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 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 sought.

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 engaged in rendering services. τhe ad飞忧e and strategies contained herein rnay not be suitable for 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 Wyatt.一一2nd ed.

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

A catalogue record for this book is available from the British

ISl日-l' 978-0-470-7份 12375 (HIB) 978-0-470平 12368 (P!B)

τypeset in 10/12 Times-Roman by Laserwords Private Limited, Chennai, India

2008033269

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

http:/

/www.ch

em4a

ll.vn

first Marrian 飞在rho

Marria口，…2007， a

,di 的部

(a c gLvr主

se ih t

巨

C

LHa

stc 7￥&'也

拿雹霉

-A

&zt c a

to

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

Co吕立f盟ts

Preface lX

General References XI

2. Basic and 3. Strategy 1: The Order of Events 4. One-Group C-X Dìsconnections 5. Strate2:v II:

Synthesis of Aromatic 7730J55310J733i751Q/30/ li233458678QJAVG12233

212i$1·EAli2·

豆

'1

6. 7.

C-X DisconnectÎons III: Reversal of Polarity , of

8. Arnìn已生 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:

(Alkynes) 15. Alkene 16. Strategy VII: 盯se of 17.τwo-Group C…C Disconnections 1: Diels-Ald时 Reactions

18. Strate2:v VIII: Introduction to 在isconnections II:

IX: Control in Car柱。nvl Condensations Compounds 19.

20.

21. C-C Disconnections III: Compounds Conjugate (Michael) Addîtion and Robinson Annelation

22. X: 技itro

23. 在NφGroup Disconnections IV: Compounds 24.

25. Disconnections V: 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

151

161

167 177 185

193

199

207

217 229 237

245

31. XIV:

http:/

/www.ch

em4a

ll.vn

VH呈

33. XV:τhe U se of Ketenes in

34. Five-Mem如ered

35. StrateQ.v XVI:

36. Six-Membered Rings

37. General Strategy C: 38. XVII: 39. AromatÍC

40. General D:A母vanced

Index

Contents

Special Methods

Synthesis

251 255

2岳 1

269 279 289

301

313

325

http:/

/www.ch

em4a

ll.vn

Preface

In the 26 years since 有iley publìshed Organic 1于ze Disconnection Approach 色y Stuart Warren，由自 approach 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 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. 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. One source of new material is the courses 出at the authors in the pharmaceutical

Our 色asic course is 'The Disconnection Approach' and the 削aterial we have for this course has reinforced our attempts to reasons for the of the various compounds which we 忧lieve enlivens the 加ok and makes it more for students. We to

a second edítíon of the workbook after the publication of the 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 Cαrbonyl 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.

Stuart 飞可arren and Paul 研rya生在

March 2008.

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn

http:/

/www.ch

em4a

ll.vn