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
收藏
页码：2147 / 2152
页数：6
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