Synthesis of sulfur compounds by the aid vinyl ethers and acetylene Communication 11. Ion-catalyzed reactions of ethyl vinyl sulfide

Abstract

1. The ion-catalyzed reactions of ethyl vinyl sulfide with water, with ethanol, with hydrogen chloride, and with hydrogen bromide have been studied, and it has been shown that addition occurs in the direction required by Markovnikov's rule, i.e. as in the similar reactions of vinyl ethers. 2. The conditions have been determined for the hydrolysis of ethyl vinyl sulfide. It has been shown that its hydrolysis by a weakly acid solution of NH2OH. HCl is much slower than that of ethyl vinyl ether. Ethyl vinyl sulfide undergoes hydrolytic decomposition when treated with a solution of HCl in a mixture of water and dioxane. acetaldehyde and acetaldehyde diethyl mercaptal being obtained. 3. A study has been made of the conditions required for the addition of alcohol to ethyl vinyl sulfide with formation of a monothioacetal. Some of the properties of the monothioacetal have been studied. 4. The conditions required for the hydrohalogenation of ethyl vinyl sulfide have been determined. The addition of hydrogen chloride and of hydrogen bromide has been affected with formation of the ethyl 1-haloethyl sulfides in about 80% yield. It has been shown that ethyl 1-haloethyl sulfides are hydrolyzed by water in the cold, with quantitative formation of hydrogen halide, acetaldehyde, and acetaldehyde diethyl mercaptal.