Advanced Organic Chemistry Part B: Reactions and Synthesis
Since its original appearance in 1977, Advanced Organic Chemistry has maintained its place as the premier textbook in the field, offering broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text
- PDF / 72,486,778 Bytes
- 1,345 Pages / 522 x 720 pts Page_size
- 5 Downloads / 236 Views
Part B: Reactions and Synthesis
Advanced Organic Chemistry PART A: Structure and Mechanisms PART B: Reactions and Synthesis
Advanced Organic FIFTH EDITION Chemistry Part B: Reactions and Synthesis FRANCIS A. CAREY and RICHARD J. SUNDBERG University of Virginia Charlottesville, Virginia
123
Francis A. Carey Department of Chemistry University of Virginia Charlottesville, VA 22904
Richard J. Sundberg Department of Chemistry University of Virginia Charlottesville, VA 22904
Library of Congress Control Number: 2006939782 ISBN-13: 978-0-387-68350-8 (hard cover) ISBN-13: 978-0-387-68354-6 (soft cover)
e-ISBN-13: 978-0-387-44899-2
Printed on acid-free paper. ©2007 Springer Science+Business Media, LLC All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer Science+Business Media, LLC, 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now know or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. 9 8 7 6 5 4 3 2 (corrected 2nd printing, 2008) springer.com
Preface The methods of organic synthesis have continued to advance rapidly and we have made an effort to reflect those advances in this Fifth Edition. Among the broad areas that have seen major developments are enantioselective reactions and transition metal catalysis. Computational chemistry is having an expanding impact on synthetic chemistry by evaluating the energy profiles of mechanisms and providing structural representation of unobservable intermediates and transition states. The organization of Part B is similar to that in the earlier editions, but a few changes have been made. The section on introduction and removal of protecting groups has been moved forward to Chapter 3 to facilitate consideration of protecting groups throughout the remainder of the text. Enolate conjugate addition has been moved from Chapter 1 to Chapter 2, where it follows the discussion of the generalized aldol reaction. Several new sections have been added, including one on hydroalumination, carboalumination, and hydrozirconation in Chapter 4, another on the olefin metathesis reactions in Chapter 8, and an expanded discussion of the carbonyl-ene reaction in Chapter 10. Chapters 1 and 2 focus on enolates and other carbon nucleophiles in synthesis. Chapter 1 discusses enolate formation and alkylation. Chapter 2 broadens the discussion to other carbon nucleophiles in the context of the generalized aldol reaction, which includes the Wittig, Peterson, and Julia olefination reactions. The chapter considers the stereochemistry of the aldol reaction in some detail, incl
