Organophosphorus Reagents
Organophosphorus ReagentsOrganophosphorus Reagents: A Practical Approach in ChemistryOrganophosphorus Reagents
A Practical Approach in Chemistry
by Patrick J. Murphy
Product Details
Oxford University Press (Sep 2004)
289 pages; numerous line drawings;
ISBN13: 978-0-19-850262-3
ISBN10: 0-19-850262-1
Description
Organophosphorus Chemistry: A Practical Approach in Chemistry provides a practical introduction to the field by mixing a brief review of the subject area with key experimental details and sample procedures. Phosphorus is an element that has been central to the development of our modern way of life. Its chemistry plays a key role in the development of such important areas as pharmaceuticals, agrochemicals, modern materials and molecular biology. Much of this work requires a sound understanding of the organic chemistry of phosphorus and this volume is designed to instruct the reader in the essential methodology used. Topics covered include phosphines, applications of phosphorus (III) and (V) compounds as reagents in synthesis, the chemistry of phosphorus ylides, applications of the Wittig reaction in the synthesis of heterocyclic and carbocyclic compounds, preparation of Iminophosphoranes and their synthetic applications in the aza-Wittig reaction, phospho-transfer processes leading to [P-C] bond formation, low valent phosphorus compounds and phosphorus methods in oligonucleotide chemistry. It is intended not only for the specialist in organophosphorus chemistry, but also for the organic chemist with little experience in the field who wishes to add phophorus-based techniques to his or her ensemble of synthetic methods.
Contents
List of contributors xi
1. Organophosphorus chemistry 1
Patrick J. Murphy
1. Introduction 1
2. Nomenclature 1
3. Practical methods 2
References 12
2. The synthesis and applications of phosphines 15
Matthew L. Clarke and Jonathan M. J. Williams
1. Introduction 15
2. Preparation of tertiary phosphines 18
3. Preparation and reactivity of primary and secondary phosphines 26
4. Polydentate phosphines and macrocycles 32
5. Chiral phosphines 35
6. Synthesis and applications of phosphines in environmentally
benign catalysis 42
7. Applications of phosphines in catalysis 45
References 48
3. Applications of phosphorus (III) and (V) compounds as reagents in synthesis 51
R. Alan Aitken and Nazira Karodia
1. Introduction 51
2. Deoxygenation and desulfurization reactions 51
3. Halogenation reactions 63
4. Dehydrative coupling and cyclization reactions 74
5. Sulfurization reactions 81
6. Miscellaneous reactions 87
References 95
Contents
4. The Wittig and related reactions 99
Andrew D. Abell and Michael K. Edmonds
1. Introduction 99
2. Standard reagents and procedures 104
3. Modifications to the standard reagents and procedures 111
4. Role in synthesis 116
References 126
5. Applications of the Wittig reaction in the synthesis of heterocyclic and
carbocyclic compounds 129
Rainer Schobert
1. Introduction 129
2. Ring-closure variants utilizing highly reactive ω-carbonyl-ylides 131
3. Ring-closure variants employing less reactive ω-carbonyl ylides or non-classical’ Wittig olefinations of esters and amides 137
References 148
6. Preparation and reactions of iminophosphoranes and their synthetic applications in the aza-Wittig reaction 151
J. Mike Southern and Ian A. O’Neil
1. Introduction 151
2. Preparation of iminophosphoranes 152
3. Removal of triphenylphosphine oxide 154
References 168
7. Phospho-transfer processes leading to [P−−C] bond formation 171
Matthew D. Fletcher
1. Introduction 171
2. The Michaelis–Arbuzov reaction 172
3. The Michaelis–Becker reaction 185
4. The Perkow reaction 191
5. The Abramov reaction 194
6. The Pudovik reaction 198
7. The Kabachnik–Fields reaction 204
8. Conjugate additions of phosphorus(III) reagents 208
References 210
8. Low-coordinated phosphorus compounds 215
Sven Asmus, Uwe Bergsträßer, Heinrich Heydt,
Marion Schmitz and Manfred Regitz
1. Introduction 215
2. Phosphorus compounds having coordination number 1 217
3. Phosphorus compounds having coordination number 2 223
References 233
9. Phosphorus methods in
nucleotide chemistry 237
David M. Williams and Vicki H. Harris
1. Introduction 237
2. Outline of chemistry 237
3. Synthesis 241
4. Analysis and purification 264
Acknowledgements 271
References 271
Index 273
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