Polyalkylene sulfides. X. The reaction of hexamethylenedithiol with 1,3‐butadiene¹

Abstract

Abstract Hexamethylenedithiol and 1,3‐butadiene react in an emulsion system in the presence of peroxides to produce 1,6‐dicrotylmercaptohexane. Hexamethylenedithiol and 1,6‐dicrotylmercaptohexane did not yield a polymer by either bulk or emulsion techniques which confirms earlier work that a sulfur atom beta to a double bond prevents free radical initiated addition of a mercaptan to that bond. Hexamethylenedithiol does give a polymer with bicrotyl showing that a buried double bond will react. Polymerizations of hexamethylenedithiol with both biallyl ether and bis‐10‐hendecen‐1‐yl ether will take place, but they show that an oxygen atom beta to a double bond inhibits the free radical catalyzed addition of a mercaptan to that bond.