Synthesis of the cyanohydrin of methyl perfluoroheptyl ketone and reaction of the ketone with hydrogen cyanide

Abstract

Abstract 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 dimethyl-formamide, 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(perfluoroheptyl)-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