P. Singh, L. Field, B. Sweetman
Sep 1, 1988
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Journal
Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract Based on 1,4-dithiols, the seven-membered cyclic trisulfide 1,5-dihydro-2,3,4-benzotrithiepin (3), the nonbenzenoid counterpart (17), related oxides, and open-chain analogs were investigated. The monoxide 4a, n=1, of 3 upon oxidation lost sulfur and gave 1,4-dihydro-2,3-benzodithiin-2-monoxide (12a, n=1). The 2,2-dioxide (4b, n=2) could not be isolated; only 4a, 12a, or 1,4-dihydro-2,3-benzodithiin-2,2-dioxide (12b, n=2) could be obtained. With related open-chain disulfides in the benzo series of the structure 1,2-(RSSCH2)2C6H4, when R was—(CH2)4SO2Na, ca. 50% disproportionation occurred in H2O in ca. 0.5 h, but the unsymmetrical disulfides with R=p-CH3C6H4- or HOCH2CH(OH)CH2- were relatively stable. The nonbenzenoid counterpart of 3, i.e. 4,7-dihydro-1,2,3-trithiepin (17) could not be obtained pure from the appropriate dichloride (19a), Bunte salt 16a or thiosulfonate (22a), nor could be the disulfide counterpart of 17, i.e. 3,6-dihydro-1.2-dithiin (23), be oxidized to the 1,1-dioxide 24. Bisdis...