6πe- versus 8πe- Electrocyclization of 1-Aryl- and Heteroaryl-Substituted (1Z,3Z)-1,3,5-Hexatrienes: A Matter of Aromaticity

被引：14

作者：

Garcia-Rubin, Silvia ^{[1
]}

Varela, Jesus A. ^{[1
]}

Castedo, Luis ^{[1
]}

Saa, Carlos ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

6+2 CYCLOADDITIONS; 8-MEMBERED RINGS; CONSTRUCTION; ALKENES; PALLADIUM; CASCADE; ALKYNES; 1,3-DIENES; 1,6-DIYNES; SYSTEMS;

D O I：

10.1021/ol802925q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Peri selectivity of the electrocyclization of 1-aryl- and heteroaryl-substituted (1Z,3Z)-1,3,5-hexatrienes, obtained by Ru-catalyzed linear coupling of 1,6-diynes to Z-propenyl(hetero)arenes, can be efficiently modulated depending on the aromaticity of the (hetero)arene: 1,3,5-hexatrienyl(hetero)arenes give 8 pi e(-) electrocyclization with the exception of 1,3,5-hexatrienylbenzenes, which give 6 pi e(-) electrocyclization.

引用

页码：983 / 986

页数：4

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