Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 25, Pages 8983-8990Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo026223k
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B3LYP/aug-cc-pVDZ and MP2/6-31+G* calculations of the reactions of HS- with small cyclic disulfides (dithiirane, 1,2-dithietane, 1,2-dithiolane, and 1,2-dithiane) were performed to determine the reaction mechanism. For the five- and six-membered rings, the reaction proceeds via the addition-elimination pathway, consistent with acyclic analogues. The smaller, more strained three and four-membered rings react by the S(N)2 mechanism. Addition of the nucleophile cannot be accommodated by the small rings without concomitant ring cleavage.
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