Radical Hydrometalation of Functional Ethylenic Compounds: Radical Autoinhibition Changes the Regioselectivity
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- 作者：Abdelkrim El Kadib ; Amal Feddouli ; Pierre Riviè ; re ; Fabien Delpech ; Monique Riviè ; re-Baudet ; Annie Castel ; Mohamed Ahra ; Aissa Hasnaoui ; Francisco Burgos ; Juan M. Manriquez ; and Ivone Chav
- 刊名：Organometallics
- 出版年：2005
- 出版时间：January 31, 2005
- 年：2005
- 卷：24
- 期：3
- 页码：446 - 454
- 全文大小：227K
- 年卷期：v.24,no.3(January 31, 2005)
- ISSN：1520-6041
文摘
Hydrometalation of carbon-carbon double bonds by group 14 hydrides is inhibited bycarbonyl compounds-mainly by 
,
-unsaturated carbonyl groups-as efficiently as byclassical radical trapping compounds, such as galvinoxyl and hydroquinone. This phenomenon, in the case of polyfunctional C=C- and C=O-containing compounds, such as carvone,leads to an autoinhibition of the exocyclic alkenylic hydrometalation under normal reactionconditions, while under drastic conditions, the O-metalation of the ,-unsaturated carbonylgroup occurs.
,-unsaturated carbonyl groups-as efficiently as byclassical radical trapping compounds, such as galvinoxyl and hydroquinone. This phenomenon, in the case of polyfunctional C=C- and C=O-containing compounds, such as carvone,leads to an autoinhibition of the exocyclic alkenylic hydrometalation under normal reactionconditions, while under drastic conditions, the O-metalation of the ,-unsaturated carbonylgroup occurs.