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organic synthesis the disconnection approach PDF

342 Pages·2009·7.38 MB·English
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Organic Synth岱is: The Disconnection Approach n v . l l a 4 m e h c . w w w / / : p t t h n v . l l a 4 m e h c . w w w / / : p t t h Organic Synth臼is; The Disconnection Approach Edition 2日d n v Stuart 飞毛Tarre室主 . Department, llu瓦 a 4 and m Paul Wyatet h Schoolof c of Bristol, U瓦 . w w w / / : p t t h ⑧WIL盯 AJohn飞iVìleyand Sons, Ltd" Publication 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1Sand Patents Act 1988. Al\ rights reserved. N 0 P缸tof 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ptas by the UK Copyright, Designs and Patents Act 1988噎 without the prior permissíon of the publisher. 认Tileyalso publishes its books in a variety of electronic formats. Some content that appears in print may not be avaHable in electronic books. n Designations used by companies to distinguish their products are often daimed as vtrademarks. AH brand names and product names used in this book are trade 凶m时, service marks, trademarlk.s or registered trademarks of their respective owners‘ The publìsher is not associated with any product ora lv念ndor mentioned in this book. 丁his publicatìon is designed to accurate and authoritative information4 in regard to the subject matter covered. It is sold on the understanding that the publisher is not engaged in rendering professional services. If m advice or other expert揣在istance is require丛 the services of cornpetent professional should be sought. e The publísher and the author make no representations or warhranties with respect to the accuracy or cornpleteness of the contents of this work and呼机ifically disclai凯 all wcarranties, without limitation any implied warranties of岳tnessfor a particular purpose. This wor.k sold with the understanding that the pubhsher is not engaged in rendering services. τhe ad飞忧we and strategies contained herein rnay not be suitable for every situation. In view of ongoing research, equwiprnent modifications, changes in govemmental regulation笃, and the constant fiow of information relating to the use of experimental reagents, equipment警 anddevices, the reader is u塔ed to review and evaluate the informatiwon provided in the packagεinsert or instructions for each chemical, piece of equipment, reagent, or device fo/r, arno只gother things‘ any changes in the instructions or índication of usage and for added wamings and prec/autions. The fact that an organization or Website is referred to in this : work as a citation andJor a potentialp source of further informatìon does not mean that the author or the publisher endorses the information the orgatnization or Website may pro飞lideor recornmendations it may rnake. Furth时, t readers should be aware that hInternet 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.一一2nded. 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 2008033269 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 Printed and bound in Great Britain by CPI Antony Rowe, Chippenham, Wiltshire ac stc Mafrirrsita n 飞在rho &拿雹霉z-At¥&'也 7 Lt巨Hiahs gec ( 的 ad, i to L v 部 Marria口,…2007, a C r主 n v . l l a 4 m e h c . w w w / / : p t t h n v . l l a 4 m e h c . w w w / / : p t t h Co吕立f盟ts Preface lX General References XI 7730J55310J733i751Q/30/ 2. Basic and Synthesis of Aromatic li233458678QJAVG12233 3. Strategy 1: The Order of Events n 4. One-Group C-X Dìsconnections v 5. Strate2:v II: l. l 6. C-X DisconnectÎons a 4 7. III: Reversal of Polarity, of m 8. Arnìn已 生 Strategy IV: Protecting e h 10. One Group C C Disconnections 1: Alcohols … c 11. General St栩如前r A: a Disconnect.ion 12. Strate玄v V: w w w 2 1 2 15. Alkene // i$1· 16. Strategy VII: 盯se of p: (Alkynes) EAli 17.τwo-Group C…C Disconntections 1: Diels-Ald时 Reactions 2· t 18. Strate2:v VIII: Introduchtion to 19. 在isconnections II: Compounds 豆 20. IX: Control in Car柱。nvl Condensations '1 21. C-C Disconnections III: Compounds Conjugate (Michael) Addîtion and Robinson Annelation 151 22. X: 技itro 161 23. 在NφGroup Disconnections IV: Compounds 167 24. 177 25. Disconnections V: 185 26. Strategy XII: Reconnection 193 27. Two-Group C…C Disconn巳ctions VI: 199 28. General B: Strategy of Car七onyl Disconnections 207 29. XIII: Introduction to Synthesis: Saturated 217 30. Three品lernbered 229 31. XIV: 237 245 VH呈 Contents 33. XV:τhe U se of Ketenes in 251 34. Five-Mem如ered 255 35. StrateQ.v XVI: Special Methods 2岳1 36. Six-Membered Rings 269 37. General Strategy C: Synthesis 279 38. XVII: 289 39. AromatÍC 301 40. General D:A母vanced 313 Index 325 n v . l l a 4 m e h c . w w w / / : p t t h 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。okís 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 nunderstand in the 1980s and what are to understand now. This second editionv is intended to fill some of . those gaps. l l The of the book is the same in the second edítioan. It alternates chapters 4 new concepts wÌth strategy chapters that put 出e new work in the context of overall planning. m 丁he 40 chapters have the same titles: some have hardly been changed whíle others have a revision with considerabele amounts of new m剖erial. In most cases from recent years are included. h One source of new material is the courses 出actthe authors in the pharmaceutical . Our 色asic course is 'The Disconnection Apwproach' and the 削aterial we have for this course has reinforced our attempts to reasons for the of the various compounds w which we 忧lieve enlivens the 加ok and makes it more for students. We to w a second edítíon of the workbook after the publication of the The 民rstedition of th巳 textbo/o/kwas in fact thεthird in a series of品。oks on : by 乳 The firspt: The an lntroduction to 如 1974, is a t book asking for a of interaction with the reader who t was to solve prho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. n v . l l a 4 m e h c . w w w / / : p t t h

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One approach to organic synthesis is retrosynthetic analysis. With this approach a chemist will start with the structure of their target molecule and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting mater
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