Theoretical study of electroreductive intramolecular coupling of nonconjugated olefinic and aromatic ketones

被引：6

作者：

Kise, N ^{[1
]}

机构：

[1] Tottori Univ, Fac Engn, Dept Biotechnol, Tottori 6808552, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 06期

关键词：

D O I：

10.1021/jo0356255

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electroreductive cyclization of hept-6-en-2-one, octa-7-en-2-one, and 5-phenylpentan-2-one was investigated by ab initio (UHF/6-311++G**) and density functional (UB3LYP/6-311++G**) calculation methods. The high regio- and stereoselectivities previously reported for olefinic ketones (exo-trans) and 5-arylpentan-2-ones (endo-trans) were reconfirmed. These experimental results well agree with the computational outcome for the transition states in the intramolecular coupling of ketyl radicals generated by one-electron transfer to the ketones.

引用

页码：2147 / 2152

页数：6

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[41] Epoxide formation by indirect electroreductive coupling between aldehydes or ketones and activated gem-dichloro compounds [J].

Oudeyer, S ;

Léonel, E ;

Paugam, JP ;

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[42] ELECTROORGANIC CHEMISTRY .8. INTRAMOLECULAR CYCLOADDITION OF NONCONJUGATE OLEFINIC KETONES TO FORM CYCLIC TERTIARY ALCOHOLS [J].

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