Thiono Compounds. 1. Interactions of Monoatomic Sulfur, Including Insertion into S-H Bonds

Article abstract of DOI:10.1021/jo00145a009

Possible traps for monoatomic sulfur were assessed by determining the reduction in yields of cyclohexanethiol (6) when carbonyl sulfide was photolyzed in cyclohexane containing the potential trap; the identity of 6 was confirmed by GC/MS and other means.Reduction of the yield of 6 by benzene, triethylamine, acetic acid, acetonitrile, and ethanol indicates undesirability of lone pair and ? systems in the assessment procedure.In order of promise as traps, compounds tested were n-Bu3SnH > (n-C5H11S)2 ca.= RSH > (EtO)3SiH > Et3SiH ca.= cyclohexane.Insertion of sulfur was demonstrated with two thiols, chosen as members of one of the most promising classes, by identity with authentic samples of derivatives of the hydrodisulfides generated; this result points to the chemical feasibility of postulated insertions of monoatomic sulfur in biological reactions and also suggests promise of the other potential traps for further study.