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Organic Synth臼is;The Disconnection Approach2日d EditionvnStuart 飞毛Tarre室主andm4all.u瓦Department,hePaul Wyattof Bristol ,http://www.cSchoolof⑧WIL盯AJohn 飞iVìley and Sons, Ltd" PublicationU瓦

This edition first published 20082008 John 飞的 ley & Sons , Inc.Registered 01.声& SonsJohn 皆ileyLtd, τheChichester,有部 t Suss帜,Atrium , Southem Gate.P0198S龟 UnitedKingdomFor details of our global 时itorial offices , for customer services and for infonnation about how to apply forpermission to 陀use the copyri在ht material in this book please see our website at www.wiley.com.τheright of the author to be identified as the author of this work has been asserted in accordance with theCopyright , 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 , inbyany fom1 or by any means , electronic , mechanical , photocopying , recording or otherwise , exc巳pt asthe UK Copyright , Designs and Patents Act 1988 噎 without the prior permissíon of the publisher.认Tileyvnalso publishes its books in a variety of electronic formats. Some content that appears in print may not beavaHable in electronic books.m4all.Designations used by companies to distinguish their products are often daimed as trademarks. AH brand namesand product names used in this book are trade 凶m时, service marks , trademarks or registered trademarks oftheir respective owners The publìsher is not associated with any product or v念ndor mentioned in this book. 丁hispublicatìon is designed toaccurate 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. Ifadvice or other expert 揣在 istance is require丛 the services of cornpetent professional should be sough t.‘http://www.cheThe publísher and the author make no representations or warranties with respect to the accuracy or cornpletenessof the contents of this work and 呼机ifically disclai 凯 all warranties ,without limitation any impliedwarranties of 岳tness for a particular purpose. This work sold with the understanding that the pubhsher is notservices. τhe ad飞忧e and strategies contained herein rnay not be suitable forengaged in renderingevery situation. In view of ongoing research , equiprnent modifications , changes in govemmental regulation笃, andthe constant fiow of information relating to the use of experimental reagents , equipment警 and devices , the readeris 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 ofusage and for added wamings and precautions. The fact that an organization or Website is referred to in thiswork as a citation andJor a potential source of further informatìon does not mean that the author or the publisherendorses 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 promotionalstatements for this work. Neither the publisher nor the author shall be liable for any damages arising herefrom.LibraηI0/ CongressC.αtaloging-in-Pl blicationDataWarren哩 StuartG.Organic synthesís : the disconnection approach I Stuart Warren and Paulp. 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 micL 百yatt, PauL n. 在tle.QD262.W2842008547'.2-dc22Wyatt.一一 2nded.2008033269A catalogue record for this book is available from the BritishISl日-l' 978-0-470-7份 12375 (HIB)τypeset978-0-470平 12368(P!B)in 10/12 Times-Roman by Laserwords Private Li mited , Chennai , IndiaPrinted and bound in Great Britain by CPI Antony Rowe, Chippenham, Wiltshire

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Co吕立f盟tsPrefacelXGeneral ReferencesXIBasicandStrategy 1: The Order of EventsOne-Group C-X DìsconnectionsStrate 2: v II:C-X DisconnectÎ onsIII: Reversal of Polarity ,7730J5531li23345867vnSynthesis of Aromaticm4all.2.3.4.5.6.7.8.ofArnìn已he生 Strategy IV: Protecting10. One Group C C Disconnections 1: Alcohols11. General St栩如前r A:a Disconnection12. Strate玄v V:VII: 盯setpht技itro23. 在NφGroup Disconnections IV:Compounds24.Disconnections V:25.26. Strategy XII: Reconnection27. Two-Group C C Disconn巳ctions VI:28. GeneralB: Strategy of Car七onyl Disconnections29.XIII: Introduction toSynthesis: Saturated30. Three品lernberedXIV:3 1.'1X:豆22.://(Alkynes)ofC C Disconnections 1: Diels-Ald时 ReactionsStrate 2: v VIII: Introduction to在isconnections II:CompoundsIX: Control in Car柱。nvl CondensationsC-C Disconnections III:CompoundsConjugate (Michael) Addîtion and Robinson Annelation17.τwo-Group18.19.20.21.ww15. Alkene16. Strategy212i 1·EAli2·w.c 151161167177185193199207217229237245

ContentsVH呈33.XV:τhe Use of Ketenes in34. Five-Mem如 ered35. Strate Q. v XV I:251255Special Methods2岳 136.37.38.39.40.Six-Membered RingsGeneral Strategy C:XVII:AromatÍCD:A母 ww.chem4all.vn325

Prefacepublìshed Organic1于ze Disconnection Approach 色y Stuartto the learning of synthesis has becomewhile the book Ìtselfis now dated in content and appearance ‘ In唱Tiley published Organicand Control by Paul Wyatt and Stuart 轧Tarren. Thís muc如柱。ok ísas afourth year und巳 rgradu时es and research workers in universities and industry. Theworkbook was published ìn 2008.τ如is new book made thεold one look very dated ínand content andgaps between what students were expectεd to understand in the 1980sto understand now. This second edition is intended to fill some ofand whatarethose gaps.Theof thebook is the same in the second edítion. It alternates chaptersnew concepts wÌth strategy chapters that put 出e new work in the context of overall planning.丁he 40 chapters have the same titles: somehave hardly been changed whíle othershavearevision with considerable amounts of new m剖erial. In most casesfrom recent years are included.in the pharmaceuticalOne source of new material is the courses 出at the authorsOur 色asic course is 'The Disconnection Approach' and the 削aterial we havefor thisof the various compoundscourse has reinforced our attempts toreasons for thefor students. Wetowhich we 忧 lieve enlivens the 加ok and makes it moreafter the publication of thea second edítíon of the workbookThe 民rst edition of th巳 textbook was in fact thεthird in a series of 品。oks onby 乳The firs t: Thean lntroduction to如 1974 , is abook asking for aof interaction with the reader whowasto solve pro剖ems whilerarely usenow as themethod has 岳阳 n suplersedt d 七 y interactive programmes on computers. Paul Wyatt is writín革 anelectronic book to replace The Cα rbonyl Group which willaof an electronic七ook and 七ooks with associated workbooks in a uniform format that we hope will prove ofvalue as students of organicdevelop their careers.In the 26 yearssince 有ileyhttp://www.chem4all.vnWarren ,由自 approachStuart飞可arrenand Paul 研rya生在March 2008.

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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。okís as a

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