THE CHEMICAL STABILITY OF THE S-METHYL XANTHATES OF SOME SIMPLE ALCOHOLS

Publisher Website
Google Scholar
Abstract
N-Octadecyl S-methyl xanthate, m.p. 38–39°, and n-hexadecyl S-methyl xanthate, m.p. 28–28.5°, were prepared for the first time, and were used to study the behavior of the S-methyl xanthate group toward reagents commonly used in research on carbohydrates. Although stable to some conditions of acetylation, hydrolysis, and methanolysis, the S-methyl xanthate group was destroyed by all methylating agents tried, with the exception of nitrosomethylurethane. The latter reagent converted a sodium xanthate salt in high yield to the S-methyl ester. Octadecyl and hexadecyl S-methyl xanthates when oxidized with hydrogen peroxide yielded crystalline substances of composition C20H40O4S2 and C18H36O4S2, respectively, whose structures were not determined. These substances each contained three additional oxygen atoms. Various attempts to estimate the S-methyl xanthate group by oxidation with bromine or periodic acid, or by reduction to methyl iodide, were unsuccessful.