Photochemistry (SPR Photochemistry (RSC)) (Vol 31)

460 Pages·2000·31.71 MB·English

by  Andrew Gilbert

Photochemistry
Volume 31
A Specialist Periodical Report
Photochemistry
Volume 31
A Review of the Literature Published between
July 1998 and June
I999
Senior Reporter
A. Gilbert Department of Chemistry,
University of Reading, UK
Reporters
Allen Manchester Metropolitan University, UK
N.S.
A. Cox , University of Warwick, UK
1. Dunkin University of Strathclyde, Glasgow, UK
A. Harriman University of Newcastle upon Tyne, UK
W.M. Horspool University of Dundee, UK
A.C. Pratt Dublin City University, Ireland
RSeC
ROYAL SOCIETY OF CHEMISTRY
ISBN 0-85404-425-6
ISSN 0556-3860
Copyright 0T he Royal Society of Chemistry
All rights reserved
Apart from any fair dealing for the purposes of research or private study, or criticism or review
as permitted under the terms of the UK Copyright, Designs and Putents Act, 1988, this
publicution may not be reproduced, stored or transmitted, in any form or by any means,
without the prior permission in writing of The Royal Society of Chemistry, or in the cuse of
reprographic reproduction only in accordance with the terms of the licences issued by the
uppropriute Reproduction Rights Organizution outside the UK. Enquiries concerning
reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at
the address printed on this puge.
Published by The Royal Society of Chemistry,
Thomas Graham House, Science Park, Milton Road, Cambridge CB4 OWF, UK
For further information see our web site at www.rsc.org
Typeset by Computape (Pickering) Ltd, Pickering, North Yorkshire, UK
Printed and bound by Athenaeum Press Ltd, Gateshead, Tyne and Wear, UK
ISBN 0-85404-425-6
ISSN 0556-3860
Copyright 0T he Royal Society of Chemistry
All rights reserved
Apart from any fair dealing for the purposes of research or private study, or criticism or review
as permitted under the terms of the UK Copyright, Designs and Putents Act, 1988, this
publicution may not be reproduced, stored or transmitted, in any form or by any means,
without the prior permission in writing of The Royal Society of Chemistry, or in the cuse of
reprographic reproduction only in accordance with the terms of the licences issued by the
uppropriute Reproduction Rights Organizution outside the UK. Enquiries concerning
reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at
the address printed on this puge.
Published by The Royal Society of Chemistry,
Thomas Graham House, Science Park, Milton Road, Cambridge CB4 OWF, UK
For further information see our web site at www.rsc.org
Typeset by Computape (Pickering) Ltd, Pickering, North Yorkshire, UK
Printed and bound by Athenaeum Press Ltd, Gateshead, Tyne and Wear, UK
Contents
Introduction and Review of the Year 1
By Andrew Gilbert
Part I Physical Aspects of Photochemistry 13
Photophysical Processes in Condensed Phases 15
By Anthony Harriman
1 Introduction 15
2 General Aspects of Photophysical Processes 15
3 Kinetic and Theoretical Considerations 17
4 Photophysical Processes in Liquid or Solid Media 18
4.1 Detection of Single Molecules 19
4.2 Radiative and Non-radiative Decay Processes 19
4.3 Amplitude or Torsional Motion 20
4.4 Quenching of Excited States 21
4.4.1 Electron-transfer Reactions 21
4.4.2 Energy-transfer Reactions 22
4.5 Photophysics of Fullerenes 23
5 Applications of Photophysics 24
6 Advances in Instrument Design and Utilization 26
References 28
Part I1 Organic Aspects of Photochemistry 45
Chapter 1 Photolysis of Carbonyl Compounds 47
By William M. Horspool
1 Norrish Type I Reactions 47
Photochemistry, Volume 3 1
0T he Royal Society of Chemistry, 2000
V
vi Contents
2 Norrish Type I1 Reactions 50
2.1 1,5-Hydrogen Transfer 50
2.2 Other Hydrogen Transfers 55
3 Oxetane Formation 57
4 Miscellaneous Reactions 61
4.1 SET Processes 61
4.2 Decarbonylation and Decarboxylation 64
4.3 Reactions of Miscellaneous Haloketones and Acid
Chlorides 67
4.4 Other Fission Processes 69
References 71
Chapter 2 Enone Cycloadditionsa nd Rearrangements: Photoreactions
of Dienones and Quinones 75
By William M. Horspool
1 Cycloaddition Reactions 75
1.1 Intermolecular Cycloaddition 75
1.1.1 Open-chain Systems 75
1.1.2 Additions to Cyclopentenones and Related
Systems 76
1.1.3 Additions to Cyclohexenones and Related
Systems 80
1.2 Intramolecular Additions 81
1.2.1 Intramolecular Additions to Cyclopentenones 83
1.2.2 Additions to Cyclohexenones and Related
Systems 83
2 Rearrangement Reactions 86
2.1 a,P-Unsaturated Systems 86
2.1,l Isomerisation 86
2.1.2 Hydrogen Abstraction Reactions 86
2.1.3 Rearrangement Reactions 87
2.2 P,y-Unsaturated Systems 88
2.2.1 The Oxa Di-n-methane Reaction and Related
Processes 88
3 Photoreactions of Thymines and Related Compounds 89
3.1 Photoreactions of Pyridones 89
3.2 Photoreactions of Thymines etc. 90
3.3 Miscellaneous Processes 93
Con tents vii
4 Photochemistry of Dienones 93
4.1 Cross-conjugated Dienones 93
4.2 Linearly Conjugated Dienones 95
5 1,2-, 1,3- and 1,4-Diketones 96
5.1 Reactions of 1,2-Diketones and other 1,2-Dicarbonyl
Compounds 96
5.2 Reactions of 1,3-Diketones 99
5.3 Reactions of 1,4-Diketones 100
5.3.1 Phthalimides and Related Compounds 101
5.3.2 Fulgides and Fulgimides 103
6 Quinones 104
6.1 o-Quinones 104
6.2 p-Quinones 104
References 106
Chapter 3 Photochemistry of Alkenes, Alkynes and Related Compounds 112
By William M. Horspool
1 Reactions of Alkenes 112
1.1 cis,trans-Isomerisation 112
1.1.1 Stilbenes and Related Compounds 113
1.1.2 The Dithienylethene System and Related
Compounds 116
1.2 Miscellaneous Reactions 120
1.2.1 Addition Reactions 120
1.2.2 Electron Transfer Processes 122
1.2.3 Other Processes 122
2 Reactions Involving Cyclopropane Rings 124
'2.1 The Di-n-methane Rearrangement and Related
Processes 124
2.1.1 The Aza-di-n-methane Rearrangement and
Related Processes 125
2.1.2 SET Induced Reactions 125
2.2 Miscellaneous Reactions Involving Three-membered
Ring Compounds 127
3 Reactions of Dienes and Trienes 128
3.1 Vitamin D Analogues 132
4 (2+2)-Intramolecular Additions 133
...
Vlll Contents
5 Dimerisation 134
6 Miscellaneous Reactions 137
6.1 Reactions Involving Cations and Radicals 137
6.2 Miscellaneous Rearrangements and Bond Fission
Processes 138
References 140
Chapter 4 Photochemistry of Aromatic Compounds 145
By Alan Cox
1 Introduction 145
2 Isomerisation Reactions 145
3 Addition Reactions 154
4 Substitution Reactions 163
5 Cyclisation Reactions 165
6 Dimerisation Reactions 171
7 Lateral Nuclear Shifts 175
8 Miscellaneous Photochemistry 176
References 182
Chapter 5 Photo-reduction and -oxidation 193
By Alan Cox
1 Introduction 193
2 Reduction of the Carbonyl Group 193
3 Reduction of Nitrogen-containing Compounds 202
4 Miscellaneous Reductions 205
5 Singlet Oxygen 209
6 Oxidation of Aliphatic Compounds 21 1
7 Oxidation of Aromatic Compounds 217