Dynamic Origin of the Stereoselectivity of a Nucleophilic Substitution Reaction

被引：52

作者：

Bogle, Xavier S. ^{[1
]}

Singleton, Daniel A. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 10期

关键词：

POSSIBLE PATH BIFURCATION; TRANSITION-STATE; SELECTIVITY; MECHANISM; PREDICTION;

D O I：

10.1021/ol300817a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2528 / 2531

页数：4

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