Torquoselectivity induced by lone-pair conjugation in the electrocyclic reactions of 1-azapolyenes

被引：37

作者：

Walker, MJ ^{[1
]}

Hietbrink, BN ^{[1
]}

Thomas, BE ^{[1
]}

Nakamura, K ^{[1
]}

Kallel, EA ^{[1
]}

Houk, KN ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 20期

关键词：

D O I：

10.1021/jo010466f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Torquoselectivity in the electrocyclic interconversions of 1-azapolyenes. and their heterocyclic isomers was investigated theoretically. The ring openings of 1,2-dihydroazete, 1,2-dihydropyridine, and 1,2-dihydroazocine were examined using HF, MP2, and B3LYP calculations. A large preference for inward rotation of the nitrogen lone pair and outward rotation of the N-H group was found for the four- and six-electron. systems. No strong preference was observed for the eight-electron system.

引用

页码：6669 / 6672

页数：4

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