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Dynamic origin of the stereoselectivity of a nucleophilic substitution reaction.

ABSTRACT: A nucleophilic substitution on a dichlorovinyl ketone was studied experimentally and computationally. A mixture of products is observed experimentally, but a conventional computational analysis does not account for the formation of the minor stereoisomer. Instead, the product mixture is predicted accurately from a dynamic trajectory study on a bifurcating energy surface. The dynamic origin of the stereoselectivity of the reaction is discussed.

SUBMITTER: Bogle XS

PROVIDER: S-EPMC3417076 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Dynamic origin of the stereoselectivity of a nucleophilic substitution reaction.

Bogle Xavier S XS Singleton Daniel A DA

Organic letters 20120427 10

A nucleophilic substitution on a dichlorovinyl ketone was studied experimentally and computationally. A mixture of products is observed experimentally, but a conventional computational analysis does not account for the formation of the minor stereoisomer. Instead, the product mixture is predicted accurately from a dynamic trajectory study on a bifurcating energy surface. The dynamic origin of the stereoselectivity of the reaction is discussed. ...[more]

PMID: 22540965

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