REACTION OF BU2CULI.LII WITH ALKYL IODIDES - EVIDENCE FOR FREE-RADICALS AND ELECTRON-TRANSFER

被引：37

作者：

BERTZ, SH

DABBAGH, G

MUJSCE, AM

机构：

[1] AT&T Bell Laboratories, Murray Hill

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 02期

关键词：

D O I：

10.1021/ja00002a035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of iodocyclohexane with Bu2CuLi.LiI yields substantial amounts of butylcyclohexane, cyclohexane, cyclohexene, bicyclohexyl, and octane. Trapping experiments demonstrate that the bulk of these products derive from cyclohexyl radicals, indicating that an electron-transfer mechanism is operative. Some of the cyclohexane and bicyclohexyl is traced to transmetalation. Likewise, 1-methyl-1-cyclohexyl iodide and 2-heptyl iodide react via electron transfer, whereas cyclohexyl bromide, 1-heptyl iodide, and 1-heptyl bromide do not. These results are in harmony with House's hypothesis that electron transfer from organocuprates occurs when the reduction potentials of the substrates are more positive than -2.35 V.

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页码：631 / 636

页数：6

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