Comprehensive Organic Synthesis. Oxidation

1007 Pages·2007·25.95 MB·english

by  LEY S. V. (Ed.)

COMPREHENSIVE
ORGANIC SYNTHESIS
Selectivity, Strategy & Effiiency
in Modern Organic Chemistry
Editor-in-Chief
BARRY M. TROST
Stanford University, CA, USA
Deputy Editor-in-Chief
IAN FLEMING
University of Cambridge, UK
Volume 7
OXIDATION
Volume Editor
STEVEN V. LEY, FRS
Imperial College of Science, Technology & Medicine, London, UK
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British Library Cataloguing in Publication Data
Comprehensive organic synthesis
3. Organic compounds. Synthesis
I. Trost, Barry M. (Barry Martin) 1941-
547.2
Comprehensive organic synthesis: selectivity, strategy and
efficiency in modern organic chemistry/editor[s] Barry M,
Trost. Ian Fleming.
p. cm.
Includes indexes.
Contents: Vol. I. - 2. Additions to C-X[pi]-Bonds - v. 3.
Carbon-carbon sigma-Bond formation - v. 4. Additions
to and substitutions at C-C[pi]-Bonds - v. 5. Combining
C-C[pi]-Bonds - v. 6. Heteroatom manipulation - v. 7.
Oxidation - v. 8. Reduction - v. 9. Cumulative indexes.
3. Organic Compounds - Synthesis I. Trost, Barry M. 1941-
11. Fleming, Ian. 1935-
QD262.C535 1991
547.24~20 90-26621
ISBN-13: 978-0-08-040598-8 (V0l7)
ISBN-10: 0-08-040598-3 (V017)
ISBN- 0-08-035929-9 (set)
For information on all Pergamon publications
visit our website at books.elsevier.com
Printed and bound in The Netherlands
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Contents
Preface ix
Contributors to Volume 7 xi
Abbreviations xv
Contents of All Volumes xix
Oxidation of Unnctivated C-H Bonds
1.1 Oxidation by Chemical Methods 1
R. H. CRABTREE & A. HABIB, Yale University, New Haven, CT, USA
1.2 Oxidation by Nitrene Insertion 21
C. J. MOODY, Loughborough University of Technology, UK
1.3 Oxidation by Remote Functionalization Methods 39
R. BRESLOW, University of Columbia, New York, NY, USA
1.4 Oxidation by Microbial Methods 53
S. M. BROWN, IC1 Specialties Research Centre, Manchester, UK
Oxidation of Activated C 4Bo nds
2.1 Oxidation Adjacent to C==C Bonds, 83
P. C. BULMAN PAGE & T. J. McCARTHY, University of Liverpool, UK
2.2 Oxidation Adjacent to C-X Bonds by Dehydrogenation 119
D. R. BUCKLE & I. L. PINTO, SmithKline Beecham Pharmaceuticals, Epsom, UK
2.3 Oxidation Adjacent to C-X Bonds by Hydroxylation Methods 151
A. B. JONES, Merck Sharp & Dohme Research Laboratories, Rahway, NJ, USA
2.4 Oxidation Adjacent to Sulfur 193
M. KENNEDY & M. A. McKERVEY, University College Cork, Republic of Ireland
2.5 Oxidation Adjacent to Nitrogen 217
H. W. PINNICK, Bucknell University, Lewisburg, PA, USA
2.6 Oxidation Adjacent to Oxygen of Ethers 235
C. R. A. GODFREY, IC1 Agrochemicals, Bracknell, UK
2.7 Oxidation Adjacent to Oxygen of Alcohols by Chromium Reagents 25 1
S. V. LEY & A. MADIN, Imperial College of Science, Technology & Medicine,
London, UK
2.8 Oxidation Adjacent to Oxygen of Alcohols by Activated DMSO Methods 29 1
T. V. LEEt, University of Bristol, UK
2.9 Oxidation Adjacent to Oxygen of Alcohols by Other Methods 305
G. PROCTER, University ofsarford, UK
2.10 Vinylic and Arylic C-H Oxidation 329
P. J. DUDFIELD, Schering Agrochemicals, Sapon Walden, UK
2.1 1 Synthesis of Quinones 345
P. J. DUDFIELD, Schering Agrochemicals, Sanon Walden, UK
Oxidation of C - CB onds
3.1 Addition Reactions with Formation of Carbon-Oxygen Bonds: 357
(i) General Methods of Epoxidation
A. S. RAO, National Chemical Laboratory, Pune, India
V
vi Contents
3.2 Addition Reactions with Formation of Carbon-Oxygen Bonds: 389
(ii) Asymmetric Methods of Epoxidation
R. A. JOHNSON, The Upjohn Company, Kalamazoo, MI, USA
& K. B. SHARPLESS, Massachusetts Institute of Technology, Cambridge, MA, USA
3.3 Addition Reactions with Formation of Carbon-Oxygen Bonds: 437
(iii) Glycol Forming Reactions
A. H. HAINES, University of East Anglia, Norwich, UK
3.4 Addition Reactions with Formation of Carbon-Oxygen Bonds: 449
(iv) The Wacker Oxidation and Related Reactions
J. TSUJI, Okayama University of Science, Japan
3.5 Addition Reactions with Formation of Carbon-Nitrogen Bonds 469
J. E. G. KEMP, Pfzer Central Research, Sandwich, UK
3.6 Addition Reactions with Formation of Carbon-Sulfur or CarbonSelenium Bonds 5 15
K. A. SWISS & D. C. LIOTTA, Emory University, Atlanta, GA, USA
3.7 Addition Reactions with Formation of Carbon-Halogen Bonds 527
S. TORI1 & T. INOKUCHI, Okayama University, Japan
3.8 Cleavage Reactions 54 1
D. G. LEE & T. CHEN, University of Regina, Canada
Oxidation of C-X Bonds
4.1 Oxidation of Carbon-Boron Bonds 593
A. PELTER & K. SMITH, University College Swansea, UK
4.2 Oxidation of Carbon-Metal Bonds 613
W. KITCHING, University of Queensland, St Lucia, Australia
4.3 Oxidation of Carbon-Silicon Bonds 641
E. W. COLVIN, University of Glasgow. UK
4.4 Oxidation of Carbon-Halogen Bonds 653
S. N. KILENYI, Sanoji Research, Brussels, Belgium
Oxidation of C-CB onds
5.1 The Baeyer-Villiger Reaction 67 1
G. R. KROW, Temple University, Philadelphia, PA, USA
5.2 The Beckmann and Related Reactions 689
D. CRAIG, Imperial College of Science, Technology & Medicine, London, UK
5.3 Glycol Cleavage Reactions 703
T. K. M. SHING, The Chinese University of Hong Kong, Hong Kong
5.4 The Hunsdiecker and Related Reactions 717
D. CRICH, University of Illinois, Chicago, IL, USA
Oxidation of Heteroatoms
6.1 Oxidation of Nitrogen and Phosphorus 735
T. L. GILCHRIST, University of Liverpool, UK
6.2 Oxidation of Sulfur, Selenium and Tellurium 757
S. UEMURA, Kyoto University, Japan
Special Topics
7.1 Oxidation by Electrochemical Methods 789
T. SHONO, Kyoto University, Japan
7.2 Oxidative Rearrangement Reactions 815
M. F. SCHLECHT, Du Pont Agricultural Products, Newark, DE, USA
Contents vii
7.3 Solid-supported Oxidants 839
P. LASZLO, Ecole Polytechnique,P alaiseau, France and Universitt!d e Lidge,
Belgium
7.4 Electron-transfer Oxidation 849
J. K. KOCHI, Universiry of Houston, 7X,U SA
Author Index 89 1
Subject Index 959
Preface
The emergence of organic chemistry as a scientific discipline heralded a new era in human develop
ment. Applications of organic chemistry contributed significantly to satisfying the basic needs for food,
clothing and shelter. While expanding our ability to cope with our basic needs remained an important
goal, we could, for the first time, worry about the quality of life. Indeed, there appears to be an excellent
correlation between investment in research and applications of organic chemistry and the standard of liv-
ing. Such advances arise from the creation of compounds and materials. Continuation of these contribu-
tions requires a vigorous effort in research and development, for which information such as that provided
by the Comprehensives eries of Pergamon Press is a valuable resource.
Since the publication in 1979 of Comprehensive Organic Chemistry, it has become an important first
source of information. However, considering the pace of advancements and the ever-shrinking timeframe
in which initial discoveries are rapidly assimilated into the basic fabric of the science, it is clear that a
new treatment is needed. It was tempting simply to update a series that had been so successful. However,
this new series took a totally different approach. In deciding to embark upon Comprehensive Organic
Synthesis, the Editors and Publisher recognized that synthesis stands at the heart of organic chemistry.
The construction of molecules and molecular systems transcends many fields of science. Needs in
electronics, agriculture, medicine and textiles, to name but a few, provide a powerful driving force for
more effective ways to make known materials and for routes to new materials. Physical and theoretical
studies, extrapolations from current knowledge, and serendipity all help to identify the direction in which
research should be moving. All of these forces help the synthetic chemist in translating vague notions to
specific structures, in executing complex multistep sequences, and in seeking new knowledge to develop
new reactions and reagents. The increasing degree of sophistication of the types of problems that need to
be addressed require increasingly complex molecular architecture to target better the function of the re-
sulting substances. The ability to make such substances available depends upon the sharpening of our
sculptors’ tools: the reactions and reagents of synthesis.
The Volume Editors have spent great time and effort in considering the format of the work. The inten-
tion is to focus on transformations in the way that synthetic chemists think about their problems. In terms
of organic molecules, the work divides into the formation of carbon+arbon bonds, the introduction of
heteroatoms, and heteroatom interconversions. Thus, Volumes 1-5 focus mainly on carbon-carbon bond
formation, but also include many aspects of the introduction of heteroatoms. Volumes 6-8 focus on
interconversion of heteroatoms, but also deal with exchange of carbon-carbon bonds for carbon-
heteroatom bonds.
The Editors recognize that the assignment of subjects to any particular volume may be arbitrary in
part. For example, reactions of enolates can be considered to be additions to C-C +bonds. However,
the vastness of the field leads it to be subdivided into components based upon the nature of the bond-
forming $ocess. Some subjects will undoubtedly appear in more than one place.
In attacking a synthetic target, the critical question about the suitability of any method involves selec-
tivity: chemo-, regio-, diastereo- and enantio-selectivity. Both from an educational point-of-view for the
reader who wants to learn about a new field, and an experimental viewpoint for the practitioner who
seeks a reference source for practical information, an organization of the chapters along the theme of
selectivity becomes most informative.
The Editors believe this organization will help emphasize the common threads that underlie many
seemingly disparate areas of organic chemistry. The relationships among various transformations
becomes clearer and the applicability of transformations across a large number of compound classes
becomes apparent. Thus, it is intended that an integration of many specialized areas such as terpenoid,
heterocyclic, carbohydrate, nucleic acid chemistry, etc. within the more general transformation class will
provide an impetus to the consideration of methods to solve problems outside the traditional ones for any
specialist.
In general, presentation of topics concentrates on work of the last decade. Reference to earlier work,
as necessary and relevant, is made by citing key reviews. All topics in organic synthesis cannot be
treated with equal depth within the constraints of any single series. Decisions as to which aspects of a
ix
X Preface
topic require greater depth are guided by the topics covered in other recent Comprehensive series. This
new treatise focuses on being comprehensive in the context of synthetically useful concepts.
The Editors and Publisher believe that Comprehensive Organic Synthesis will serve all those who
must face the problem of pnparing organic compounds. We intend it to be an essential reference work
for the experienced practitioner who seeks information to solve a particular problem. At the same time,
we must also serve the chemist whose major interest lies outside organic synthesis and therefore is only
an occasional practitioner. In addition, the series has an educational role. We hope to instruct experi-
e n d i nvestigators who want to leam the essential facts and concepts of an area new to them. We also
hope to teach the novice student by providing an authoritative account of an area and by conveying the
excitement of the field.
The need for this series was evident from the enthusiastic response from the scientific community in
-
the most meaningful way their willingness to devote their time to the task. I am deeply indebted to an
exceptional board of editors, beginning with my deputy editor-inchief Ian Fleming, and extending to the
-
entire board Clayton H. Heathcock, Ryoji Noyori, Steven V. Ley, Leo A. Paquette, Gerald Pattenden,
Martin F. Semmelhack, Stuart L. Schreiber and Wehard Winterfeldt.
The substance of the work was cwited by over 250 authors from 15 countries, illustrating the truly in-
ternational nature of the effort. I thank each and every one for the magnificent effort put forth. Finally,
such a work is impossible without a publisher. The continuing commitment of Pergamon Press to serve
the scientific community by providing this Comprehensive series is commendable. Specific credit goes
to Colin Drayton for the critical role he played in allowing us to realize this work and also to Helen
Mcpherson for guiding it through the publishing maze.
A work of this kind, which obviously summarizes accomplishments, may engender in some the feel-
ing that there is little more to achieve. Quite the opposite is the case. In looking back and seeing how far
we have come, it becomes only more obvious how very much more we have yet to achieve. The vastness
of the problems and opportunities ensures that research in organic synthesis will be vibrant for a very
long time to come.
BARRY M.T ROST
Palo Alto, Califolnia
Contributors to Volume 7
Professor R. Breslow
Department of Chemistry, University of Columbia, New York, NY 10027, USA
Dr S. M. Brown
IC1 Fine Chemicals, PO Box A38, keds Road, Huddersfreld, Yorkshire HD2 IFF, UK
Dr D. R. Buckle
SmithKline Beecham Pharmaceuticals, Biosciences Research Centre, Great Burgh,
Yew Tree Bottom Road, Epsom, Surrey KT18 SXQ, UK
Dr P. C. Bulman Page
Department of Chemistry, University of Liverpool, PO Box 147, Liverpool L69 3BX, UK
Dr T. Chen
Department of Chemistry, Luther College, University of Regina, Regina, Saskatchewan S4S OM,
Canada
Dr E. W. Colvin
Department of Chemistry, University of Glasgow, Glasgow G12 SQQ, UK
Professor R. H. Crabtree
Department of Chemistry, Yale University, PO Box 6666, New Haven, CT 0651 1-811 8, USA
Dr D. Craig
Department of Chemistry, Imperial College of Science, Technology 8c Medicine, South Kensington,
London SW7 2AY, UK
Dr D. Crich
Department of Chemistry (WC 11l ), University of Illinois at Chicago, Box 4348, Chicago, IL 60680,
USA
Dr P. J. Dudfield
Schering Agrochemicals Ltd, Chesterford Park Research Station, Saffron Walden, Essex CBlO IXL, UK
Dr T. L. Gilchrist
Department of Chemistry, University of Liverpool, PO Box 147, Liverpool L69 3BX, UK
Dr C. R. A. Godfrey
IC1 Agrochemicals, Jealott's Hill Research Station, Bracknell, Berks RG12 6EY, UK
Dr A. Habib
Department of Chemistry, Yale University, PO Box 6666, New Haven, CT 0651 1-81 18, USA
Dr A. H. Haines
School of Chemical Sciences, University of East Anglia, Norwich NR4 7JT, UK
Dr T. Inokuchi
Department of Applied Chemistry, School of Engineering, Okayama University, Tsushima-naka 3,
Okayama 700, Japan
Dr R. A. Johnson
Hypersensitivity Diseases Research, The Upjohn Company, Kalamazoo, MI 49001-0199, USA
Dr A. B. Jones
Merck Sharp & Dohme Research Laboratories, PO Box 2000, R8OM-119, Rahway, NJ 07065, USA
Dr J. E. G. Kemp
Wizer Central Research, Sandwich, Kent CT13 9NJ, UK
Dr M. Kennedy
Department of Chemistry, University College Cork, Republic of Ireland
Dr S. N. Kilenyi
Sanofi Research, Avenue de Bejar, B-1120 Brussels, Belgium
Dr W. Kitching
Department of Chemistry, University of Queensland, St Lucia, Queensland 4067, Australia
xi
xii Contributors to Volume 7
Professor J. K. Kochi
Department of Chemistry, University of Houston, University Park, 4800 Calhoun Road, Houston,
TX 77204-564 1, USA
Professor G. R. Krow
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA
Professor P. Laszlo
Laboratoire DCFI, &ole Polytechnique, F-9128 Palaiseau Cedex, France
Professor D. G. Lee
Department of Chemistry, Luther College, University of Regina, Regina, Saskatchewan S4S OA2,
Canada
Dr T. V. Leet
Department of Chemistry, University of Bristol, Bristol BS8 lTS, UK
Professor S. V. Ley
Department of Chemistry, Imperial College of Science, Technology & Medicine, South Kensington,
London SW7 2AY, UK
Professor D. C. Liotta
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, GA 30322, USA
Dr A. Madin
Department of Chemistry, Imperial College of Science, Technology & Medicine, South Kensington,
London SW7 2AY, UK
Mr T. J. McCarthy
Department of Chemistry, University of Liverpool, Po Box 147, Liverpool L69 3BX, UK
Professor M. A. McKervey
Department of Chemistry, University College Cork, Republic of Ireland
Professor C. J. Moody
Department of Chemistry, University of Technology, Loughborough, Leicestershire LE1 1 3TU. UK
Professor A. Pelter
Department of Chemistry, University College Swansea, Singleton Park, Swansea SA2 8PP, UK
Professor H. W. Pinnick
Department of Chemistry, Bucknell University, Lewisburg, PA 17837, USA
Dr I. L. Pinto
SmithKline Beecham Phmaceuticals, Biosciences Research Centre, Great Burgh,
Yew Tree Bottom Road, Epsom, Surrey KT18 SXQ, UK
Professor G. Procter
Department of Chemistry & Applied Chemistry, University of Salford, Salford M5 4WT,U K
Dr A. S. Rao
Emeritus Scientist, Organic Chemistry Division, Indian Institute of Chemical Technology,
Hyderabad 500 007, India
Dr M. F. Schlecht
E I Du Pont de Nemours & Co., Inc., Agricultural Products Department, Stine-Haskell Research Center,
PO Box 30, Newark, DE 19714, USA
Professor K. B. Sharpless
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Dr T. K. M. Shing
Department of Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong
Professor T. Shono
Institute for Chemical Research, Kyoto University, Uji, Kyoto-fu 61 1, Japan
Professor K. Smith
Department of Chemistry, University College Swansea, Singleton Park, Swansea SA2 8PP. UK
Contributors to Volume 7 xiii
Dr K. A. Swiss
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, GA 30322, USA
Professor S. Toni
Department of Applied Chemistry, School of Engineering, Okayama University, Tsushima-naka 3,
Okayama 700, Japan
Professor J. Tsuji
Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700, Japan
Professor S. Uemura
Institute for Chemical Research, Kyoto University, Uji, Kyoto-fu 61 1, Japan