Merging of 4+2 and 2+4 cycloaddition paths in the regiospecific dimerization of methacrolein. A case of concerted crypto-diradical cycloaddition

被引：31
|
作者：
Toma, L
Romano, S
Quadrelli, P
Caramella, P
机构：
[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
[2] Univ Pavia, Ist Nazl Fis Mat, I-27100 Pavia, Italy
[3] Univ Pavia, Dipartimento Fis A Volta, I-27100 Pavia, Italy
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 30期
关键词：
methacrolein; dimerization; secondary orbital interactions;
D O I：
10.1016/S0040-4039(01)00891-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regiospecific dimerization of methacrolein takes place through a very asynchronous and symmetrical transition structure, which shows a merging of the 4+2 and 2+4 cycloaddition paths. The geometrical features of the transition structures correspond well to a case of diradical formation. A cage of secondary orbital interactions restricts the flexibility of the diradical transition structure and stabilizes it. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5077 / 5080
页数：4
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