The Reactions of Amines and Sulfur with Olefins. III. The Reaction of Diethylamine and Sulfur with 1,5-Diolefins

Abstract 2,6-Dimethylocta-2,6-diene (I) with the sulfur-diethylamine combination at 140° C yields mainly saturated cross-linked sulfides, R⋅Sx⋅R , where R contains thiacyclopentane groups adjacent to the sulfide cross-link ( x=1 or 2), together with the cyclic sulfides (II) and (VI), (VII), and (VIII), formed by the intramolecular sulfuration of (I). Infrared spectroscopic evidence suggests the occurrence of similar cyclic structures in squalene polysulfide and in ebonite.