CONCOMITANT EPOXIDE DEOXYGENATION AND DEACETYLATION OF GLYCIDYL ACETATES INDUCED BY TELLURIDE ION

被引：26

作者：

DITTMER, DC

ZHANG, Y

DISCORDIA, RP

机构：

[1] Department of Chemistry, Center for Science and Technology, Syracuse University, Syracuse, New York 13244

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 05期

关键词：

D O I：

10.1021/jo00084a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of glycidyl acetates with telluride ion (Te2-) produced by reduction of elemental Te with LiEt(3)BH yields allylic alcohols by loss of the epoxide oxygen atom and the acetyl group from the ester. If the glycidyl acetate is disubstituted at C-3, a rearrangement to an isomeric allylic alcohol competes with the deoxygenation-deacetylation. Triethylborane, a byproduct in the reduction of Te, is believed to play an important role as a Lewis acid since when it is absent or removed by addition of fluoride ion the reaction is extremely slow.

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页码：1004 / 1010

页数：7

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