Journal of Organic Chemistry p. 4651 - 4654 (1982)
Update date:2022-08-03
Topics:
Field, Lamar
Ravan, J. Valerie
Dunkel, John D.
Waites, John A.
White, David W.
et al.
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.
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