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Book Details
Abstract
Organophosphorus chemistry is a very broad and exciting field, with potential opportunities to the researchers involved in multi-disciplinary areas of scientific endeavour including organic, medicinal, pharmaceutical, agricultural and industrial chemistry. Coverage in this annual review of the literature presents a comprehensive and critical survey of the vast field of study involving organophosphorus compounds. With reviews covering phosphines and phosphonium salts through to tervalent and quinquevalent phosphorus acid derivatives, nucleotides, ylides, and phosphazenes. Since synthetic organic chemists have been motivated to develop eco-friendly methodologies for generating phosphorus-functionalized compounds of potential interest, the Editors have added to the usual content with a timely chapter on the recent developments in green synthetic approaches in organophosphorus chemistry to reflect the current interests in the area. This book continues the series with a timely overview of this interesting and developing field.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Contents | ix | ||
| Preface | v | ||
| Phosphines and related C–P bonded compounds | 1 | ||
| 1 Introduction | 1 | ||
| 2 Phosphines | 1 | ||
| 2.1 Preparation | 1 | ||
| 2.1.1 From halogenophosphines and organometallic reagents | 1 | ||
| 2.1.2 From metallated phosphines | 3 | ||
| 2.1.3 By the addition of P-H to unsaturated compounds | 6 | ||
| 2.1.4 By the reduction of phosphine oxides and related compounds | 7 | ||
| 2.1.5 Miscellaneous methods of preparing phosphines | 10 | ||
| 2.2 Reactions | 14 | ||
| 2.2.1 Nucleophilic attack at carbon | 14 | ||
| 2.2.2 Nucleophilic attack at halogen | 18 | ||
| 2.2.3 Nucleophilic attack at other atoms | 19 | ||
| 2.2.4 Miscellaneous reactions | 25 | ||
| 3 pπ-Bonded phosphorus compounds\r | 26 | ||
| 4 Phosphirenes, phospholes and phosphinines | 30 | ||
| References | 35 | ||
| Tervalent phosphorus acid derivatives | 51 | ||
| 1 Introduction | 51 | ||
| 2 Halogenophosphorus compounds | 51 | ||
| 3 Tervalent phosphorus amides | 54 | ||
| 3.1 Aminophosphines | 54 | ||
| 3.2 Phosphoramidites | 61 | ||
| 3.3 Phosphorodiamidites | 67 | ||
| 4 Tervalent phosphorus esters | 70 | ||
| 4.1 Phosphonites | 70 | ||
| 4.2 Phosphinites | 75 | ||
| 4.3 Phosphites | 86 | ||
| 4.4 Mixed ligands | 91 | ||
| References | 94 | ||
| Phosphine chalcogenides | 99 | ||
| References | 128 | ||
| Phosphonium salts and P-ylides | 132 | ||
| 1 Introduction | 132 | ||
| 2 Phosphonium salts | 132 | ||
| 2.1 Synthesis and characterisation | 132 | ||
| 2.2 Applications in synthesis | 136 | ||
| 2.3 Medical and biological applications | 140 | ||
| 2.4 Miscellaneous applications | 142 | ||
| 3 Phosphonium-based ionic liquids (PILs) | 143 | ||
| 3.1 Preparation and characterisation | 143 | ||
| 3.2 Applications in synthesis | 146 | ||
| 3.3 Extraction and separation technologies based on PILs | 147 | ||
| 3.4 Electrochemical applications | 149 | ||
| 3.5 Miscellaneous applications | 150 | ||
| 4 P-ylides (phosphoranes) | 152 | ||
| 4.1 Preparation, structural properties and mechanistic investigations | 152 | ||
| 4.2 Applications in synthesis | 153 | ||
| 4.3 Coordination chemistry | 156 | ||
| References | 158 | ||
| Nucleotides and nucleic acids: mononucleotides | 170 | ||
| 1 Introduction | 170 | ||
| 2 Nucleoside mono-, di- and triphosphates | 170 | ||
| 2.1 Synthesis | 170 | ||
| 2.2 Biochemical findings | 178 | ||
| 3 Nucleoside phosphonates | 182 | ||
| 4 Nucleotide prodrugs | 185 | ||
| 4.1 Phosphoramidate prodrugs bearing an amino acid ester residue | 185 | ||
| 4.2 Other phosphoramidate and non-amidate prodrugs | 187 | ||
| 5 Analogues of mRNA caps | 189 | ||
| 6 Fluorescently labelled probes | 191 | ||
| References | 192 | ||
| Quinquevalent phosphorus acids | 196 | ||
| 1 Introduction | 196 | ||
| 2 Phosphoric acids and their derivatives | 197 | ||
| 2.1 Synthesis of phosphoric acids and their derivatives | 197 | ||
| 2.2 Reactions of phosphoric acids and their derivatives | 213 | ||
| 2.3 Biological application of phosphoric acids and their derivatives | 226 | ||
| 2.4 Miscellaneous applications | 240 | ||
| 2.5 Phosphoric acids and their derivatives as catalysts | 241 | ||
| 2.5.1 Spirodicycloalkylphenyl derivatives | 242 | ||
| 2.5.2 Binaphthyl and (1,2,3,4-tetrahydronaphthyl) derivatives | 242 | ||
| 2.5.2.1 Bi(1,2,3,4-tetrahydronaphthyl) derivatives | 242 | ||
| 2.5.2.2 Binaphthyl derivatives | 242 | ||
| 3 Phosphonic acids and their derivatives | 264 | ||
| 3.1 Synthesis of phosphonic acids and their derivatives | 264 | ||
| 3.2 Reaction of phosphonic acids and their derivatives | 284 | ||
| 3.3 Biological application of phosphonic acids and their derivatives | 320 | ||
| 3.4 Miscellaneous applications | 333 | ||
| 4 Phosphinic acids and their derivatives | 335 | ||
| 4.1 Synthesis of phosphinic acids and their derivatives | 335 | ||
| 4.2 Reactions of phosphinic acids and their derivatives | 338 | ||
| 4.3 Biological applications of phosphinic acids and their derivatives | 340 | ||
| 4.4 Miscellaneous applications | 342 | ||
| References | 345 | ||
| Pentacoordinated and hexacoordinated compounds | 354 | ||
| 1 Introduction | 354 | ||
| 2 Pentacoordinated phosphorus compounds | 354 | ||
| 2.1 Synthesis | 354 | ||
| 2.2 Intermediates and transition states | 356 | ||
| 2.3 Structural investigations | 363 | ||
| 3 Hexacoordinated compounds | 366 | ||
| References | 374 | ||
| Phosphazenes | 375 | ||
| 1 Introduction | 375 | ||
| 2 Acyclic phosphazenes | 375 | ||
| 3 Cyclophosphazenes | 386 | ||
| 3.1 Cyclodiphosphazenes | 386 | ||
| 3.2 Chlorocyclophosphazenes | 386 | ||
| 3.3 Dendrimer-like and dendrimeric cyclophosphazenes | 388 | ||
| 3.4 Cyclophosphazene-based ligands | 405 | ||
| 3.5 Reactions of cyclophosphazenes with difunctional reagents | 413 | ||
| 4 Polyphosphazenes | 417 | ||
| 5 Hybrid systems | 422 | ||
| 6 Applications | 427 | ||
| 6.1 Flame retardancy and thermal stability | 427 | ||
| 6.2 Biomedical applications | 429 | ||
| 6.3 Catalytic and miscellaneous applications | 432 | ||
| Acknowledgments | 433 | ||
| References | 433 | ||
| Green synthetic approaches in organophosphorus chemistry: \rrecent developments with energy-efficient protocols\r | 438 | ||
| 1 Introduction | 438 | ||
| 2 Recent advances in the development of energy-efficient protocols in organophosphorus chemistry | 439 | ||
| 2.1 Synthesis of organophosphorus compounds at ambient conditions | 439 | ||
| 2.1.1 Synthesis of α-hydroxyphosphonates via the Pudovik reaction\r | 439 |