Organic Syntheses Based on Name Reactions - 2nd Edition (Tetrahedron Organic Chemistry) PDF
Preview Organic Syntheses Based on Name Reactions - 2nd Edition (Tetrahedron Organic Chemistry)
TETRAHEDRON ORGANIC CHEMISTRY SERIES Series Editors: J E Baldwin, FRS R M Williams University of Oxford, Colorado State University, Oxford, OX1 3Q Y, UK Fort Collins, CO 80523, USA VOLUME 22 Organic Syntheses Based on Name Reactions SECOND EDITION Related Pergamon Titles of Interest BOOKS Tetrahedron Organic Chemistry Series: CARRUTHERS: Cycloaddition Reactions in Organic Synthesis CLARIDGE: High-Resolution NMR Techniques in Organic Chemistry FINET: Ligand Coupling Reactions with Heteroatomic Compounds GAWLEY & AUB~_: Principles of Asymmetric Synthesis HASSNER & STUMER: Organic Syntheses Based on Name Reactions and Unnamed Reactions McKILLOP: Advanced Problems in Organic Reaction Mechanisms OBRECHT & VILLALGORDO: Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries PERLMUTTER: Conjugate Addition Reactions in Organic Synthesis SESSLER & WEGHORN: Expanded, Contracted & Isomeric Porphyrins TANG & LEVY: Chemistry of C-Glycosides WONG & WHITESIDES: Enzymes in Synthetic Organic Chemistry LI & GRIBBLE: Palladium in Heterocyclic Chemistry PIETRA: Biodiversity and Natural Product Diversity Other Series: RAHMAN: Studies in Natural Products Chemistry (series) JOURNALS BIOORGANIC & MEDICINAL CHEMISTRY BIOORGANIC & MEDICINAL CHEMISTRY LETTERS TETRAHEDRON TETRAHEDRON LETTERS TETRAHEDRON: ASYMMETRY Full details of all Elsevier Science publications are available on www. elsevier.com or from your neare,.. Elsevier Science office Organic Syntheses Based on Name Reactions SECOND EDITION A. HAS S N E R a n d C. S T U M E R Department of Chemistry Bar-Ilan University Ramat-Gan, Israel 200 2 P E R G A M O N An imprint of E lsev ier Sc ience A m s t e r d a m - Boston - London - New York - Oxford - Paris San Diego - San Franc isco - S ingapore - S y d n e y - Tokyo ELSEVIER SCIENCE Ltd The Boulevard, Langford Lane Kidlington, Oxford OX5 1GB, UK �92 002 Elsevier Science Ltd. All rights reserved. This work is protected under copyright by Elsevier Science, and the following terms and conditions apply to its use: Photocopying Single photocopies of single chapters may be made for personal use as allowed by national copyright laws. Permission of the Publisher and payment of a fee is required for all other photocopying, including multiple or systematic copying, copying for advertising or promotional purposes, resale, and all forms of document delivery. Special rates are available for educational institutions that wish to make photocopies for non-profit educational classroom use. Permissions may be sought directly from Elsevier Science via their homepage (http://www.elsevier.com) by selecting 'Customer Support' and then 'Permissions'. Alternatively you can send an e-mail to: Contents Foreword to first edition vii Foreword to second edition ix Name Reactions (arranged alphabetically) Names Index 425 Reagents Index 435 Reactions Index 441 Functional Group Transformations Index 445 This Page Intentionally Left Blank vii Non nova sed nove FOREWORD to FIRST EDITION And these are the names . . . The above are the opening words of Exodus, the second book of the Pentateuch. Already in ancient times, names were important in association with events. As organic chemistry developed during the 20 th century, researchers started associating synthetically useful reactions with the names of discovers or developers of these reactions. In many cases such names serve merely as a mnemonic, to remember a reaction more easily; there are few chemistry undergraduates who do not know what the FriedeI-Crafts reaction is. In recent years there has been a proliferation of new reactions and reagents that have been so useful in organic synthesis that often people refer to them by name. Many of these are stereoselective or regioselective methods. While the expert many know exactly what the Makosza vicarious nucleophilic substitution, or the Meyers asymmetric synthesis refers to, many students as well as researchers would appreciate guidance regarding such "Name Reactions". It is in this context that we perceived the necessity to incorporate the older name reactions with some newer name reactions or "unnamed reactions", that are often associated with a name but for which details, references and experimental details are not at everyone's fingertips. This was our inspiration for the current monograph "Organic Syntheses Based on Name Reactions and Unnamed Reactions". In particular, we thought it would be useful to include cross-references of functional group transformations and an experimental procedure, so that the reader will be able to evaluate the reaction conditions at a glance; for instance, is this reaction carried out at room temperature or at 200 ~ For 1 h or 5 days? Are special catalysts required? How is the reaction worked up, what yield can be expected? The choice of which reactions to include is not an easy one. First there are the well known "Name Reactions", that have appeared in various monographs or in the old Merck index. Some of these are so obvious mechanistically to the modern organic chemistry practitioner that we have in fact omitted them; for instance, esterification of alcohols with acid ch lor ides- the Schbtten-Baumann procedure. Others are so important and so well entrenched by name, like the Baeyer-Villiger ketone oxidation, that it is impossible to ignore them. In general, we have kept older name reactions that are not obvious at first glance. In some cases we have combined similar reactions under one heading, for instance, the Hunsdiecker-Borodin-CristoI-Firth decarboxylative bromination. It is not a simple task to decide whether credit is due to the first discoverer of a reaction or to is developer. Often an improvement on a method is more useful than the original discovery, and usually one reaction owes its inception to some previous discovery; non nova sed nove. viii Organic Syntheses Based on Name Reactions Except in the case of reactions that have been known for a long time under shared names, we often took the liberty to include in the title, as well as in the references (here to save space), only the name of the major author; for this we apologize to the co-authors, whose contributions are often seminal. For reactions named after contemporary authors, we have tried to consult the authors about choice of examples, etc. This led, for instance, to the Mannich- Eschenmoser methylination. Among the newer reactions, we have chosen those that are not only synthetically useful, but, at first glance, not immediately obvious transformations. Another criterion was the stereochemical implication of the process. Yet, we admit our own bias in choosing from the plethora of novel transformations that have appeared in the literature over the past 30 years or so. Space limitation was by necessity a criterion. Nevertheless, we have included approximately 450 name reactions and 2100 references. We sincerely apologize if we have inadvertently omitted important reactions. In all cases we have tried to include the first reported reference, a reference to an experimental procedure, and whenever possible, a review reference (journal or Organic Reactions). In general, we did not include references to books, series of monographs, or to Organic Syntheses; chemists will of course consult these where available. Furthermore, we have compiled four indices, which should be helpful to the reader: 1. A names index with cross references to multiple names; 2. A reagents index; 3. An index to types of reactions, e.g. alkylations, stereoselective reductions, cyclizations, etc.; and 4. Most important for the synthetic chemist is an index to the synthesis of functional groups, e.g., synthesis of alkenes from ketones, as well as conversion of ketones to alkenes. We thank our families for their support and understanding during the travail on this book. Special thanks are due to my son, Lawrence Hassner, for constructive suggestions and invaluable help. We are grateful to the TEVA Pharmaceutical Co. for support of this project. Alfred Hassner Carol Stumer Foreword to Second Edition The success of the first edition of "Organic Syntheses Based on Name Reactions and Unnamed Reactions" and the proliferation of new Name Reactions are the reason for this new revised edition. It became obvious that many new reagents and reactions are being referred to in the organic chemistry research community by their names. Hence, in addition to over 170 new reactions (previously referred to as Unnamed Reactions) in the first edition, we have included in the second edition 157 new Name Reactions bringing the total to 545. However, we have eliminated the term "Unnamed Reactions" from the title of the monograph, since these reactions are now no longer unnamed. Furthermore, we omitted some older and less utilized Name Reactions that appeared in the first edition but have included them in the Name Index, by providing reference to the page number in the first edition (e.g. Baudisch 1-27, refers to first edition, p.27). The new additions are all synthetically useful or not immediately obvious transformations. In choosing them, emphasis was placed on stereoselective or regioselective reagents or reactions including asymmetric syntheses. The latter are particularly timely with the recent Nobel Prize in Chemistry awarded in this area. Again we admit our own bias in choosing from the many interesting newer transformations reported in the literature. Where possible we have tried to consult with the Name Reaction major author. We apologize if inadvertently important reactions were omitted. We have maintained the useful format of providing important references (over 3,300); in each case this includes one of the first references to the reaction and a review reference where available. Furthermore, an example of an experimental procedure is provided. Important features of this monograph remain the indexes, which should be helpful to the reader: A names index with cross references to multiple names; A reagent index; A reaction index, e.g. acylations, asymmetric synthesis; epoxidation, heteroannulations, rearrangements, etc.; as well as A functional group transformation index, which allows one to search for conversions of one functional group to another. The latter has proved valuable to the synthetic chemist searching for pathways to perform such synthetic procedures. Hence, the monograph should be of interest to chemists in industry and academia. In fact this format has led to the monograph being adopted as a text in advanced organic chemistry courses. We thank our families for their understanding during the travail on this book and are grateful to TEVA Pharmaceutical Co. for their support. This monograph is dedicated to the memory of my dear wife Cyd (A.H.). Alfred Hassner Carol Stumer
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