Author:
Ginsburg Jack Leon,Darvesh Katherine Valenta,Axworthy Patricia,Langler Richard Francis
Abstract
Moller-Plesset molecular orbital calculations at the 6-31+G(d) level have
been completed on substituted dimethyl sulfide-derived carbanions. The results
are applied to the prediction of regiochemistry for chlorination of
unsymmetrical sulfides. Notwithstanding the need for future improvements,
regiochemical predictions based on stabilities of sulfur-substituted
carbanions match experimental results better than earlier predictions based on
stabilities of sulfur-substituted carbonium ions or sulfur-substituted free
radicals. The present results suggest that the mechanism for the elimination
step in the Pummerer rearrangement of a chlorosulfonium cation is an
E 1cb-like process.
Cited by
3 articles.
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