Synthesis and Reactions of 5-[Amino(thiomethyl)methylene]- 2,2-dimethyl-1,3-dioxane-4,6-dione

Abstract

5-[Amino(thiomethyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (4) is obtained from 5-[bis- (thiomethyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (1) and aqueous ammonia in excellent yield. Its reaction with m-chloroperbenzoic acid gives the sulfoxide derivative 5-[amino(sulfinylmethyl) methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (5). With triphenylphosphine, 5 reacts to give triphenyl( thiomethyl)phosphonium 5-cyano-2,2-dimethyl-1,3-dioxane-4,6-dionate (6) from which the methyltriphenylphosphonium salt 6a is obtained with excess triphenylphosphine. The crystal structures of 4, 5 and 6a are discussed.