Photochemistry_of_Organic

PHOTOCHEMISTRY OF ORGANIC COMPOUNDS

Photochemistry of Organic Compounds: From Concepts to Practice Petr Klán and Jakob Wirz © 2009 P. Klán and J. Wirz. ISBN: 978-1-405-19088-6

Postgraduate Chemistry Series

A series designed to provide a broad understanding of selected growth areas of chemistry at postgraduate student and research level. Volumes concentrate on material in advance of a normal undergraduate text, although the relevant background to a subject is included. Key discoveries and trends in current research are highlighted and volumes are extensively referenced and cross-referenced. Detailed and effective indexes are an important feature of the series. In some universities, the series will also serve as a valuable reference for final year honours students.

Editorial Board

Professor James Coxon (Editor-in-Chief), Department of Chemistry, University of Canterbury, New Zealand.

Professor Pat Bailey, Department of Chemistry, University of Keele, UK.

Professor Les Field, School of Chemistry, University of New South Wales, Sydney, Australia.

Professor Dr. John A. Gladysz, Department of Chemistry, Texas A&M University, College Station, TX, USA.

Professor Philip Parsons, School of Chemistry, Physics and Environmental Science, University of Sussex, UK.

Professor Peter Stang, Department of Chemistry, University of Utah, Utah, USA.

Titles in the Series

Protecting Groups in Organic Synthesis

James R. Hanson

Organic Synthesis with Carbohydrates

Geert-Jan Boons and Karl J. Hale

Organic Synthesis using Transition Metals

Roderick Bates

Stoichiometric Asymmetric Synthesis

Mark Rizzacasa and Michael Perkins

Catalysis in Asymmetric Synthesis (Second Edition)

Vittorio Caprio and Jonathan M. J. Williams

Reaction Mechanisms in Organic Synthesis

Rakesh Kumar Parashar

Forthcoming

Practical Biotransformations: A Beginner’s Guide

Gideon Grogan

PHOTOCHEMISTRY OF ORGANIC COMPOUNDS

From Concepts to Practice

Petr Klan

Department of Chemistry, Faculty of Science, Masaryk University Czech Republic, klan@sci.muni.cz

Jakob Wirz

Department of Chemistry, University of Basel, Switzerland

J.Wirz@unibas.ch

This edition first published 2009

# 2009 P. Klan and J. Wirz

Registered office

John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex, PO19 8SQ, United Kingdom

For details of our global editorial offices, for customer services and for information about how to apply for permission to reuse the copyright material in this book please see our website at www.wiley.com.

The right of the authors to be identified as the authors of this work has been asserted in accordance with the Copyright, Designs and Patents Act 1988.

All rights reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by the UK Copyright, Designs and Patents Act 1988, without the prior permission of the publisher.

Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic books.

Designations used by companies to distinguish their products are often claimed as trademarks. All brand names and product names used in this book are trade names, service marks, trademarks or registered trademarks of their respective owners. The publisher is not associated with any product or vendor mentioned in this book. This publication is designed to provide accurate and authoritative information in regard to the subject matter covered. It is sold on the understanding that the publisher is not engaged in rendering professional services. If professional advice or other expert assistance is required, the services of a competent professional should be sought.

The publisher and the author make no representations or warranties with respect to the accuracy or completeness of the contents of this work and specifically disclaim all warranties, including without limitation any implied warranties of fitness for a particular purpose. This work is sold with the understanding that the publisher is not engaged in rendering professional services. The advice and strategies contained herein may not be suitable for every situation. In view of ongoing research, equipment modifications, changes in governmental regulations and the constant flow of information relating to the use of experimental reagents, equipment and devices, the reader is urged to review and evaluate the information provided in the package insert or instructions for each chemical, piece of equipment, reagent or device for, among other things, any changes in the instructions or indication of usage and for added warnings and precautions. The fact that an organization or Website is referred to in this work as a citation and/or a potential source of further information does not mean that the author or the publisher endorses the information the organization or Website may provide or recommendations it may make. Further, readers should be aware that Internet Websites listed in this work may have changed or disappeared between when this work was written and when it is read. No warranty 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.

Library of Congress Cataloging-in-Publication Data

Kla´n, Petr.

Photochemistry of organic compounds : from concepts to practice / Petr Kla´n, Jakob Wirz.

p. cm.

Includes bibliographical references and index.

ISBN 978-1-4051-9088-6 (cloth : alk. paper) – ISBN 978-1-4051-6173-2 (pbk.: alk. paper)

1. Organic photochemistry. 2. Organic compounds–Synthesis. I. Wirz, Jakob. II. Title.

QD275.K53 2009 572’.435–dc22 2008044442

A catalogue record for this book is available from the British Library.

ISBN 978-1-405-19088-6 (HBK)

ISBN 978-1-405-16173-2 (PBK)

Typeset in 10/12pt Times by Thomson Digital, Noida, India.

Printed and bound in Great Britain by CPI Antony Rowe, Ltd, Chippenham, Wiltshire

This book is dedicated to our families, teachers and students

Contents

6.2.1Aromatic hydrocarbons and heterocycles: photorearrangement

6.3.2Carbonyl compounds: oxetane formation

6.3.5Carbonyl compounds: photocyclization following

6.3.8Carboxylic acids and their esters: photofragmentation