Epoxide formation by ring closure of the cinnamyloxy radical

被引：12

作者：

Amaudrut, J ^{[1
]}

Wiest, O ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 09期

关键词：

D O I：

10.1021/ol005749t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cinnamyloxy and oxiranyl benzyl radicals were generated by photolysis of alkyl 4-nitrobenzenesulfenates. The yet unprecedented epoxide ring formation from a primary alkoxy radical was observed. Experimental evidence supports the fact that the mode of ring opening of the oxiranyl carbinyl radical system is thermodynamically driven. B3LYP/6-31G* calculations indicate that the closed form of the radical is similar to 5 kcal/mol more stable than the open one.

引用

页码：1251 / 1254

页数：4

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