Abstract
Triphenylmethanethiosulfenyl chloride 1 [(C 6H 5) 3CSSCl] (and its dithio homolog 2 [(C 6H 5) 3CSSSCl]) give stable addition products (ca. 85% yield) with cyclopentene and cyclohexene. When these adducts are warmed with a diene, they deliver diatomic sulfur-trapped derivatives. These tetrasulfides are quantitatively converted to the corresponding disulfide 3 with triphenylphosphine; this affords cyclic disulfides in & 50% isolated yield from the diene. In addition, evidence has been obtained implicating dithietane intermediate 4.
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