ABSTRACT Experimental data in the last decade on the synthesis of fluoroorganic compounds by the reaction of internal perfluoroolefins with nucleophilic reagents and a direct fluorination with elementary fluorine or electrochemical fluorination of the most important classes of organic compounds have been generalized and synthesized. This overview covers the principles governing the orientation and reactivity of fluorinated alkenes towards nucleophiles, fluoride ion as a nucleophile and reactions with nitrogen-, oxygen- and sulfur-centred nucleophiles. It has been demonstrated that the reaction of internal perfluoroolefins with N-nucleophilic reagents issues in the production of terminal perfluoroolefins whose interaction leads to the formation of enamines. Factors which affect the stability and reactivity of these compounds are discussed as examples of their application for the preparation of partially fluorinated organic compounds containing N-, O-, P- and S-atoms. This treatment summarized new experimental data, as well as their theoretical description, on the use of C-nucleophiles and C-carbcations from internal perfluoroolefins in the synthesis of fluoroorganic compounds. Examples of application of the perfluorinated carbcations to the synthesis of perfluorinated olefins, cyclic systems and oxygen-containing heterocyclic compounds are considered. The mechanisms of these transformations are discussed. A new approach to the generation of the stable perfluorinated alkylradicals from internal perfluoroolefins is discussed and experimental data are given on its reaction with the varies substances. The overview discusses the modern methods for the fluorination of elementary fluorine internal perfluoroolefins and their derivatives. The problems related to the production of high quality perfluorinated organic materials are analyzed. We have also set out the trends in the development of methods and technology for obtaining fluoroorganic compounds. Instances of the practical application of various perfluorinated substances in industry and medicine are given, rational techniques for producing them are suggested and trends in the development of this technology are considered.
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