Synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-β-lactones obtained by epoxidation of 4-alkylidene-2-oxetanones

被引：14

作者：

Duffy, RJ ^{[1
]}

Morris, KA ^{[1
]}

Romo, D ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 48期

关键词：

D O I：

10.1021/ja053478h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe the first synthesis of spiroepoxy-β-lactones obtained via epoxidation of ketene dimers. These compounds display unexpected stability that may be due to a double anomeric effect garnered from analysis of bond lengths by X-ray crystallography of one spirocycle in comparison to calculated bond lengths of related structures. These new strained intermediates display interesting reactivity leading to a butenolide, an α-hydroxyketone, a triol, an α-chloroketone, and an α-azidoketone. Copyright © 2005 American Chemical Society.

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页码：16754 / 16755

页数：2

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