THE STEREOSELECTIVITY OF ADDITION OF BENZOYLOXYL RADICALS TO CYCLOHEXENES

被引:17
作者
BOTTLE, SE [1 ]
BUSFIELD, WK [1 ]
JENKINS, ID [1 ]
机构
[1] GRIFFIN HOSP,FAC SCI & TECHNOL,DERBY,CT 06418
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1992年 / 12期
关键词
D O I
10.1039/p29920002145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of benzoyloxyl radicals with cyclohexene and with 4-tert-butylcyclohexene, in the presence of the free radical scavenger 1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yloxyl, are reported. The major reaction observed was diaxial addition; however, the diequatorial and axial/equatorial products were also significant. The overall ratio of axial to equatorial addition of benzoyloxyl radicals to the alkene was 3:2. The aminoxyl trapping reaction was more selective with a ratio of trans to cis addition of ca. 4:1. The stereoselectivity of the addition of benzoyloxyl radicals to cyclohexenes and of the trapping of cyclohexyl radicals is discussed in terms of steric and polar factors.
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页码:2145 / 2150
页数:6
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