Addition Reactions of Esters of Phosphorus(III) Acids with Unsaturated Systems

A. N. Pudovik; I. V. Konovalova

doi:10.1055/s-1979-28566

Synthesis 1979; 1979(2): 81-96
DOI: 10.1055/s-1979-28566

review

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Addition Reactions of Esters of Phosphorus(III) Acids with Unsaturated Systems

A. N. Pudovik^* , I. V. Konovalova

^*Kazan Lenin State University, Arbuzov Institute of Organic and Physical Chemistry, Kazan Branch of USSR Academy of Sciences, USSR

Abstract

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This review gives a survey of the synthetically useful addition reactions of phosphorus(III) esters (phosphites, phosphonites, phosphinites, amidophosphites, etc. and their thio-analogues) with systems containing carbon-carbon, carbon-oxygen, carbon-nitrogen, nitrogen-nitrogen, nitrogen-oxygen, and nitrogen-sulphur multiple bonds. Products of these reactions are the corresponding derivatives of phosphorus(V) esters (phosphates, phosphonates, phosphinates, etc. and their thio-analogues). Emphasis has been placed on results published within the last ten years. 1. Introduction 2. Addition Reactions to C=C-Systems 2.1. Derivatives of α,β-Unsaturated Carboxylic Acids 2.2.α,β-Unsaturated Carbonyl Compounds 2.3. 1-Alkenephosphonates 2.4. α,β-Unsaturated Nitro Compounds 2.5. Alkenes, Ethynyl Esters, and Halodienes 3. Addition Reactions to C≡C-Systems 4. Addition Reactions to C=O-Systems 4.1. Aldehydes and Ketones 4.2. Activated Carbonyl Compounds 4.3. Carbonyl Compounds and Amines 5. Addition Reactions to C=N- and -C≡N-Systems 5.1. Imines 5.2. Isocyanates and Isothiocyanates 5.3. Cyanides and Isocyanides 6. Addition Reactions to -N=N-, O=N-, and S=N- Systems

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