Synthesis of carbamoylsulfenyl chloride and its derivatives

Abstract

Imine was prepared by the reaction of 2,6-diethylaniline with an excess paraformaldehyde, generated water being removed effectively with water determination apparatus. The protons of $N=CH_2$ in the imine exhibited a second-order spectrum. The imine reacted with bifuntional chloride to give N-(choromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenyl chloride. The reaction of the carbamolsulfenyl chloride with various equimolar alcohols resulted in the formation of the carbamoyl-sulfenate esters in 71-95\% yields. The corresponding carbamoyl-sulfenate esters decomposed gradually, but the thermal rearrangement of S-O bonding S=O bonding was not found. The nucleophilic attack of an exess alcohol to the carbamoylsulfenyl chloride was made on both divalent sulfur and $\alpha$-carbon of N-chloromethyl group. The corresponding substituted products were considerably stable to light.