Dynamic Origin of the Stereoselectivity of a Nucleophilic Substitution Reaction

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 ac...

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Veröffentlicht in:	Organic letters 2012-05, Vol.14 (10), p.2528-2531
Hauptverfasser:	Bogle, Xavier S, Singleton, Daniel A
Format:	Artikel
Sprache:	eng
Schlagworte:	chemical reactions energy Hydrocarbons, Chlorinated - chemistry Ketones - chemistry Lewis bases Molecular Structure organic compounds Stereoisomerism stereoisomers stereoselectivity Vinyl Compounds - chemistry
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creator	Bogle, Xavier S Singleton, Daniel A
description	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.
doi_str_mv	10.1021/ol300817a
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source	ACS Publications; MEDLINE
subjects	chemical reactions energy Hydrocarbons, Chlorinated - chemistry Ketones - chemistry Lewis bases Molecular Structure organic compounds Stereoisomerism stereoisomers stereoselectivity Vinyl Compounds - chemistry
title	Dynamic Origin of the Stereoselectivity of a Nucleophilic Substitution Reaction
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