Transition metal-catalyzed [4+2+2] cycloadditions of bicyclo[2.2.1]hepta-2,5-dienes (norbornadienes) and bicyclo[2.2.2]octa-2,5-dienes

被引：42

作者：

Chen, Y ^{[1
]}

Kiattansakul, R ^{[1
]}

Ma, B ^{[1
]}

Snyder, JK ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo010268o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transition-metal-catalyzed [4 + 2 + 2] cycloadditions of norbornadienes, bicyclo[2.2.2]octa-2,5-diene, and benzobarrelene with 1,3-butadienes proceed in excellent yields using cobalt-based catalytic systems. Two key distinctions between these [4 + 2 + 2] cycloadditions and the corresponding transition-metal-catalyzed [2 + 2 + 2] reactions of norbornadiene are the requirement of a bimetal catalytic system with a bisphosphine ligand for the former and exclusive regioselectivity in the [4 + 2 + 2] reaction of 2-substituted norbornadienes to produce 1-substituted adducts. These distinctions may indicate two distinct mechanisms for the [4 + 2 + 2] and [2 + 2 + 2] reactions.

引用

页码：6932 / 6942

页数：11

共 105 条

[1] DIMERIZATION AND TRIMERIZATION OF NORBORNADIENE BY SOLUBLE RHODIUM CATALYSTS [J].