DEMONSTRATION OF LACK OF INVERSION OF MIGRATING ALLYL GROUP IN PHOTOCHEMICAL REARRANGEMENT OF A HEXA-1,5-DIENE DERIVATIVE

被引：29

作者：

BROWN, RFC

COOKSON, RC

HUDEC, J

机构：

[1] Chemistry Department, Southampton University U.K

来源：

TETRAHEDRON | 1968年 / 24卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(01)92603-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

UV irradiation of trans-2-(3′-deuterioallyl)cyclohexylidenemalononitrile (XIa) induces rearrangement to allyl-1-cyclohexenylmalononitrile, in which the deuterium is still entirely at the 3-position of the allyl group but has lost its geometrical configuration (XIIa and b). Thermal Cope rearrangement of the mixture (XIIa and b) or of pure synthetic cis-isomer (XIIa) forms 2-(1′-deuterioallyl)cyclohexylidenemalononitrile (XIb). Since XIa recovered from incomplete irradiation is quite unchanged and the cis-isomer (XIIa) is stable to irradiation even in the presence of cyclohexylidenemalononitrile, the cis-trans equilibration must occur during the migration of the allyl group. © 1968.

引用

页码：3955 / &

共 18 条

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