The dimerisation of 2-methoxycarbonylbuta-1,3-diene: the importance of paralocalisation energy in assessing diene reactivity

被引：23

作者：

Spino, C ^{[1
]}

Crawford, J

Cui, YP

Gugelchuk, M

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

[2] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1998年 / 06期

关键词：

D O I：

10.1039/a708199e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dimerisation and competitive cycloaddition of 2-methoxycarbonylbuta-1,3-diene with electron-rich dienes has been investigated. Experimental results provide evidence that the enthalpy of the pi-system significantly influences the energy of the transition state of cycloadditions of this type. This has been corroborated by ab initio calculations. We propose an early reorganisation of the pi-electrons in such cycloadditions to explain the influence stated above.

引用

页码：1499 / 1506

页数：8

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