Oxidation of Alcohols to Aldehydes and Ketones A Guide to Current Co

This book is a must for anyone involved in the preparation of organic compounds. It is the first one in a new series on basic reactions in organic synthesis. It provides plenty of detailed and useful information in the practical aspects of the oxidation o

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BASIC REACTIONS IN ORGANIC SYNTHESIS EDITOR-IN-CHIEF: GABRIEL TOJO DEPARTMENT OF ORGANIC CHEMISTRY, FACULTY OF CHEMISTRY, UNIVERSITY OF SANTIAGO DE COMPOSTELA 15872-SANTIAGO DE COMPOSTELA SPAIN. [email protected]

Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice, by Gabriel Tojo and Marcos Ferna´ndez

Oxidation of Alcohols to Aldehydes and Ketones A Guide to Current Common Practice

GABRIEL TOJO and MARCOS FERNA´NDEZ

Authors: Gabriel Tojo Department of Organic Chemistry Faculty of Chemistry University of Santiago de Compostela 15872-Santiago De Compostela Spain

Marcos Ferna´ndez Department of Organic Chemistry Faculty of Chemistry University of Santiago de Compostela 15872-Santiago De Compostela Spain

Editor-on-Chief Gabriel Tojo Department of Organic Chemistry Faculty of Chemistry University of Santiago de Compostela 15872-Santiago De Compostela Spain

Library of Congress Control Number: 2005927383 ISBN-10: 0-387-23607-4 ISBN-13: 978-0387-23607-0 Printed on acid-free paper. ß2006 Springer ScienceþBusiness Media, Inc. All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer ScienceþBusiness Media, Inc. 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 known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks and similar terms, even if they are not identiWed as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed in the United States of America 10 9 8 7 6 5 4 3 2 1 springer.com

This book is dedicated to the thousands of scientists cited in the references that constructed our present knowledge on the oxidation of alcohols to aldehydes and ketones. Thanks to their collective eVort, the preparation of medicines, pesticides, colorants and plenty of chemicals that make life more enjoyable, is greatly facilitated.

Acknowledgements

We thank the staV of the library of the Faculty of Chemistry of the University of Santiago de Compostela (SPAIN) for their most serviceable help in collecting literature for the preparation of this book.

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Preface

There is natural selection in the synthetic organic laboratory. Successful reagents Wnd their way into specialized journals and tend to populate the researcher’s benches. Sometimes, old species like active manganese dioxide in the oxidation of unsaturated alcohols are so well adapted to a certain reaction niche that they remain unchallenged for a long time. On other occasions, a successful new species like Dess Martin’s periodinane enjoys a population explosion and very quickly inhabits a great number of laboratories. On the other hand, the literature is Wlled with promising new reagents that fell into oblivion