Solvent effects in the beta-(phosphatoxy)alkyl radical migration as revealed by deuterium labelling and H-1 NMR spectroscopy.

被引：8

作者：

Crich, D

Escalante, J

Jiao, XY

机构：

[1] Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061

[2] Univ. Autonoma del Estado de Morelos, Cuernavaca, CP 62210

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1997年 / 03期

关键词：

D O I：

10.1039/a603916b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been demonstrated through use of a deuterium labelled probe that the beta-(phosphatoxy)alkyl radical migration of la, previously shown to be non-dissociative in benzene, occurs through a fragmentation recombination mechanism in the polar, protic solvent tert-butanol. Most likely the reaction occurs through the intermediacy of a contact ion pair which does not allow crossover with an external nucleophile, Parallel experiments for the beta-(acyloxy)alkyl migration, however, Provided no evidence for a dissociative mechanism in any of the solvents tested.

引用

页码：627 / 630

页数：4

共 19 条

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