Effect of ultraviolet radiation upon the n-hexane solutions of allylic mercaptans (crotyl, prenyl and B, r, r-trimethylallyl mercaptans) was investigated. Crotyl mercaptan readily brought about self-addition in terms of a free radical chain mechanism to give sulfide thiols (2) and (3), 2, 5-diethyl-1, 4-dithiane (4) aRd 2-ethyl-5-methyl-1, 4-dithiepane (5) as dimers. Prenyl mercaptan has been reported to be selectively dimerized to 2, 5-diisopropyl-1, 4-dithiane. But in the case of B, r, r-trimethylallyl mercaptan, the corresponding dimers were not obtained. On the basis of these results, the effect of r-methyl group on allylic mercaptan was discussed.
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