Oxidation of Primary Alcohols to Carboxylic Acids A Guide to Current

This book, the second in the series Basic Reactions in Organic Synthesis, is a laboratory guide for the transformation of primary alcohols into carboxylic acids. It contains copious information on important experimental details and procedures for the succ

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Gabriel Tojo Marcos Fernández

Oxidation of Primary Alcohols to Carboxylic Acids A Guide to Current Common Practice

Oxidation of Primary Alcohols to Carboxylic Acids

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 Fernández Oxidation of Primary Alcohols to Carboxylic Acids: A Guide to Current Common Practice, by Gabriel Tojo and Marcos Fernández

Oxidation of Primary Alcohols to Carboxylic Acids A Guide to Current Common Practice

GABRIEL TOJO and MARCOS FERNÁNDEZ

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

Marcos Fernández Department of Organic Chemistry Faculty of Chemistry University of Santiago de Compostela 15872-Santiago de Compostela Spain

Editor-in-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: 2006929452 ISBN-10: 0-387-35431-X ISBN-13: 978-0387-35431-6 e-ISBN-10: 0-387-35432-8 e-ISBN-13: 978-0387-35432-3 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 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 identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. 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 who constructed our present knowledge on the oxidation of primary alcohols to carboxylic acids. Thanks to their collective effort, the preparation of medicines, pesticides, colorants, and a variety of chemicals that make life more enjoyable, is greatly facilitated.

Preface to the Series

There is natural selection in the synthetic organic laboratory. Successful reagents find their way into specialized journals and tend to populate researchers’ 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 periodinane—enjoys a population explosion and very quickly inhabits a great number of laboratories. On