SYNTHESIS OF THE CYANOHYDRIN OF METHYL PERFLUOROHEPTYL KETONE AND REACTION OF THE KETONE WITH HYDROGEN CYANIDE

Article abstract of DOI:10.1016/S0022-1139(00)85119-2

The cyanohydrin of methyl perfluoroheptyl ketone 2 was able to be synthesized by a two-step process, i.e., an addition of sodium bisulfite and subsequent treatment with sodium cyanide.When equimolar amounts of ketone 2 and sodium cyanide were reacted in water or dipolar aprotic solvent such as dimethylformamide, acetonitrile, 1,2-dimethoxyethane and tetrahydrofuran, cyclic addition products composed of two molecules of ketone 2 and one molecule of hydrogen cyanide were exclusively formed as 2,5-dimethyl-2,5-bis(perfluoroheptyl)-4-oxazolidone 6 and 2,5-dimethyl-2,5-bis(per fluoroheptyl)-1,3-dioxolane-4-one 7 instead of the cyanohydrin of ketone 2.It is conceivable that a solubility characteristic of a compound carrying a long perfluoroalkyl group is responsible for the exclusive formation of cyclic compounds 6 and 7.

Full text of DOI:10.1016/S0022-1139(00)85119-2

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