Characteristic Features of the Chemical Properties of Fluorine-containing Unsaturated Compounds

The review deals with the results obtained in the study of the chemical properties of organofluorine and saturated compounds containing the C=C, C=O, C=N, C=C=C, C=C=O, C=C=N, etc. groups. The characteristics of the reactions of fluoro-olefins and related compounds with nucleophiles as well as the methods of synthesis and the properties of fluorocarbanions (including mesomeric fluorocarbanions) are examined. The electronically amphoteric character of the C=C bond in fluorine-containing unsaturated compounds, ensuring the possibility of interaction with strong electrophiles, and the synthetic possibilities resulting from these reactions are demonstrated. The analogy between the chemical properties of polyfluoro-substituted carbonyl compounds, their derivatives, heterocumulenes, and nitro- and nitroso-compounds is discussed. The influence of fluorine atoms is manifested by the markedly electrophilic properties of these compounds and in many cases also by the singular stability of the unusual structures formed as a result of their reactions. The bibliography includes 180 references.