The reduction of organic compounds of sulfur by metals in liquid ammonia

Abstract

A systematic study of the reduction of organic sulfur compounds by different metals in liquid ammonia is reported for the first time. A metal with a high half-cell potential favors a greater extent of reduction than a lower potential metal. The greater the concentration of ammonium ion as a proton donor, the greater will be the evolution of hydrogen, and the lower will be the extent of reduction. A mechanism for the reduction of organic sulfur compounds by metals in ammonia is presented. A new procedure for the quantitative removal and determination of hydrogen sulfide in mercaptans was developed. A new synthesis for allyl mercaptan was found. The formation of a resin believed to be a thiophene polymer of the formula (C₄H₄S)x is reported.