Verification of stereospecific dyotropic racemisation of enantiopure D and L-1,2-dibromo-1,2-diphenylethane in non-polar media

被引：10

作者：

Braddock, D. Christopher ^{[1
]}

Roy, Debjani ^{[2
]}

Lenoir, Dieter ^{[3
]}

Moore, Edward ^{[1
]}

Rzepa, Henry S. ^{[1
]}

Wu, Judy I-Chia ^{[2
]}

Schleyer, Paul von Rague ^{[2
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Univ Georgia, Dept Chem, Athens, GA 30602 USA

[3] Helmholtz Ctr Munich, Inst Ecol Chem, D-85758 Neuherg, Germany

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 71期

基金：

美国国家科学基金会;

关键词：

REARRANGEMENTS; BROMINE; STILBENES;

D O I：

10.1039/c2cc33676f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of a dyotropic rearrangement of an enantio-merically pure, conformationally unconstrained, vicinal dibromide confirms theoretical predictions: D and L-1,2-dibromo-1,2-diphenyl-ethane racemise stereospecifically in refluxing benzene without crossover to the meso-isomer. An orbital analysis of this six-electron pericyclic process is presented.

引用

页码：8943 / 8945

页数：3

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