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

共 50 条

[1] ELECTROREDUCTIVE INTRAMOLECULAR COUPLING OF NONCONJUGATED AROMATIC KETONES [J].

KISE, N ;

SUZUMOTO, T ;

SHONO, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1407-1413

[2] Electroreductive intramolecular coupling of aromatic δ- and ε-keto esters [J].

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Arimoto, K ;

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[3] ELECTROREDUCTIVE COUPLING BETWEEN AROMATIC KETONES AND ENOL ESTERS [J].

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[7] Electroreductive acylation of aromatic ketones with acylimidazoles [J].

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[8] INTRAMOLECULAR REACTIONS OF OLEFINIC DIAZO KETONES [J].

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[9] Electroreductive intramolecular cyclization of olefinic esters and its application to the synthesis of muscone [J].

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Murai, Y ;

Ishifune, M ;

Masuda, H ;

Shimomura, M ;

Murase, H ;

Shono, T .

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