The Reactions of Amines and Sulfur with Olefins. I. The Reaction of Diethylamine and Sulfur with Cyclohexene

The reaction of diethylamine and sulfur with cyclohexene at 140° yields dicyclohexyl monosulfide and disulfide and also saturated polymeric products, C6H11⋅Sx⋅(C6H10)⋅Sx⋅C6H11 , containing cyclohexane units linked by sulfur, where x is 1 or 2. N-Ethylthioacetamide (IV) is formed as a major product; minor products include N,N-diethylthioacetamide (V) and diethylammonium hydrogen sulfide (VI), IV, V, and VI are formed also by the reaction of diethylamine with sulfur at 140°. The mechanisms of the olefin-sulfuration processes are discussed.