Abstract
Abstract Cyclohexene reacts with sulfur at 140° in the presence of zinc dimethyldithio-carbamate, tetramethylthiuram monosulfide, or tetramethylthiuram disulfide, to produce 2-cyclohexene-1-thiol as the major product after lithium aluminum hydride reduction of the polysulfide compounds. Secondary products are cis- and trans-1, 2-eyclohexanedithiol and cyclohexanethiol. Zinc dimethyldithiocarbamate is postulated to promote the reaction via an ionic mechanism as it causes more trans than cis-1, 2-cyclohexanedithiol to be formed. Tetramethylthiuram monosulfide and disulfide are postulated to promote the reaction via a free radical mechanism as they cause more cis- than trans-1, 2-cyclohexanedithiol to be formed.
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