Thermal disrotatory electrocyclic isomerization of cis-bicyclo[4.2.0]oct-7-ene to cis,cis-1,3-cyclooctadiene

被引：15

作者：

Baldwin, JE ^{[1
]}

Gallagher, SS

Leber, PA

Raghavan, A

机构：

[1] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA

[2] Franklin & Marshall Coll, Dept Chem, Lancaster, PA 17604 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 09期

关键词：

D O I：

10.1021/ol040022g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ratio of observed rate constants, k/k', for thermal isomerizations of cis-bicyclo[4.2.0]oct-7-ene and its 2,2,5,5-d(4) analogue to cis,cis-1,3-cyclooctadienes at 250 degreesC is 1.17, indicative of a secondary, not a primary, deuterium kinetic isotope effect. The reaction does not occur through a [1,5] hydrogen shift from the transient cis, trans-1,3-cyclooctadiene intermediate to form the observed cis,cis-diene product.

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页码：1457 / 1460

页数：4

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