X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .31. GENERATION OF NITRONES FROM OXIMES - BACKGROUND AND SCOPE OF THE TANDEM 1,2-PROTOTROPY-INTRAMOLECULAR CYCLOADDITION SEQUENCE

被引：57

作者：

GRIGG, R ^{[1
]}

HEANEY, F ^{[1
]}

MARKANDU, J ^{[1
]}

SURENDRAKUMAR, S ^{[1
]}

THORNTONPETT, M ^{[1
]}

WARNOCK, WJ ^{[1
]}

机构：

[1] QUEENS UNIV BELFAST, DEPT CHEM, BELFAST BT9 5AG, ANTRIM, NORTH IRELAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)86441-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Prototropy in aryl and aliphatic oximes generates a small equilibrium concentration of the corresponding NH nitrone. Examples of a tandem 1,2-prototropy-intramolecular cycloaddition sequence involving aryl and aliphatic oximes are described and steric and electronic factors that favour or disfavour such a sequence are discussed. Deuterium labelling studies with an aliphatic oxime rule out the involvement of an enehydroxylamine in the prototropic generation of the NH nitrone.

引用

页码：4007 / 4030

页数：24

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