REACTIVE INTERMEDIATES FROM THE SOLVOLYSIS OF MUTAGENIC O-ALKYL N-ACETOXYBENZOHYDROXAMATES

被引：34

作者：

BONIN, AM

GLOVER, SA

HAMMOND, GP

机构：

[1] UNIV NEW ENGLAND,DEPT CHEM,ARMIDALE,NSW 2351,AUSTRALIA

[2] WORKSTATE AUSTRALIA,TOXICOL UNIT,SYDNEY,NSW 2001,AUSTRALIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 06期

关键词：

D O I：

10.1039/p29940001173

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Mutagenic O-(para-substituted benzyl) N-acetoxybenzohydroxamates undergo acid-catalysed solvolysis in aqueous acetonitrile but there is a change in mechanism from A(A1)1 to E1 on going from para electron-withdrawing substituents to para +M electron-donating groups. The former permit the formation of a discrete nitrenium ion intermediate whereas the latter promote a concerted elimination of a resonance stabilized benzyl carbocation.

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页码：1173 / 1180

页数：8

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