Borodkin Y. Bis(1,1-dihydropolyfluoroalkyl)sulfides, bis(2-fluoro-2-polyfluoroalkylvinyl)sulfides and bis(polyfluoroalkylacetylenyl)sulfides. Synthesis and chemical properties.

Українська версія

Thesis for the degree of Doctor of Philosophy (PhD)

State registration number

0824U003767

Applicant for

Specialization

  • 102 - Хімія

01-09-2022

Specialized Academic Board

47679

Institute of Organic Chemistry NAS of Ukraine

Essay

The dissertation is devoted to the development of methods for the synthesis and investigation of chemical properties of bis(1,1-dihydropolyfluoroalkyl)sulfides, bis(2-fluoro-2-polyfluoroalkylvinyl)sulfides and bis(polyfluoroalkylacetylenyl)sulfides and their derivatives. Symmetric bis(polyfluoroalkyl)sulfides and sulfones are almost not represented in the literature, despite the relatively simple structure of molecules in these classes. Methods for the synthesis of new types of fluorine-containing sulfur derivatives - bis(1,1-dihydropolyfluoroalkyl)sulfides and sulfones have been developed. The study of the chemical properties of these compounds allowed us to establish the basic pattern’s of the reaction of their dehydrofluorination. Polyfluoroalkyl-containing heterocyclic compounds of classes such as 1,4-oxathiin-4,4-dioxide derivatives, 2,3-dihydro-1,4-oxathiines, 1,4-oxathian, bis(pyrazolyl)sulfones, bis(triazolyl)sulfones were synthesized and have not been presented in the literature before. The reactivity of the obtained heterocycles was studied. Bis(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorooct-1-yn-1-yl)sulfide was also obtained for the first time. The results of X-ray structural studies for representatives of almost all types of the obtained compounds are presented.

Research papers

Borodkin Ya., Rusanov E., Marchenko A., Koidan Yu., Shermolovich Yu. Synthesis and chemical properties of Di(2-fluoro-2-polyfluoroalkyl- alkenyl)sulfides and 2,6-bis(polyfluoroalkyl)-1,4-oxathiine 4,4-dioxides. Journal of Sulfur Chemistry. 2019. Vol. 40, № 4, P. 416-425. DOI: 10.1080/17415993.2019.1596269.

Borodkin Ya. S., Rusanov E. B., Khizhan A. I., Shermolovich Yu. G. Synthesis of fluorinated dipyrazolyl sulfones from bis(2-fluoro-2-polyfluoroalkylalkenyl) sulfones and diazomethane. Chemistry of Heterocyclic Compounds. 2019, Vol. 55, № 11, P. 1065–1069. DOI: 10.1007/s10593-019-02578-3.

Borodkin Ya. S., Shermolovich Yu. G. Synthesis of novel 1,4-oxathiine derivatives containing polyfluoroalkyl substituents at positions 2 and 6. Chemistry of Heterocyclic Compounds. 2021, Vol. 57, № 1, P. 69–74. DOI: 10.1007/s10593-021-02869-8.

Borodkin Ya. S., Rusanov E. B., Shermolovich Yu. G. Isomeric bis(pyrazolyl)sulfones based on bis(1,1-dihydropolyfluoroalkyl)sulfones. A new type of ligands for metal-polymer complexes with silver cation. Voprosy khimii i khimicheskoi tekhnologii 2021, Vol. 138, № 5, P. 21–29. DOI: 10.32434/0321-4095-2021-138-5-21-29.

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