SELECTIVE HOMOLYTIC CLEAVAGE OF PRIMARY OVER SECONDARY CARBON OXYGEN BONDS IN CYCLIC THIONOCARBONATES - THE EFFECT OF BOND ANGLE STRAIN-ENERGY

被引：29

作者：

ZIEGLER, FE

ZHENG, ZL

机构：

[1] Sterling Chemistry Laboratory, Yale University, New Haven

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 05期

关键词：

D O I：

10.1021/jo00292a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several cases of the selective homolytic, tri-rc-butylstannyl radical promoted fragmentation of primary over secondary carbon-oxygen bonds in 6-membered cyclic thionocarbonates have been uncovered. Molecular mechanics calculations (MM2) simulate the transition states for these reactions and have revealed that bond angle distortion is a prime contributor to the abnormal course of these reactions. © 1990, American Chemical Society. All rights reserved.

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页码：1416 / 1418

页数：3

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