Sonochemical cycloadditions of o-quinones.: The search for a cation radical pathway

被引：3

作者：

Avalos, M

Babiano, R

Bravo, JL

Cabello, N

Cintas, P ^{[1
]}

Hursthouse, MB

Jiménez, JL

Light, ME

Palacios, JC

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain

[2] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 21期

关键词：

cation radicals; Diels-Alder reactions; furans; o-quinones;

D O I：

10.1016/S0040-4039(00)00578-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder cycloadditions of an o-quinone monoketal with different furans, under argon, are considerably accelerated by ultrasonic irradiation. Moreover, these sonochemical reactions are regiospecific and proceed with a high diastereoselectivity. The results can be ascribed to the chemical role of ultrasounds which may favor a single electron transfer mechanism with respect to ionic or nonpolar pathways. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4101 / 4105

页数：5

共 27 条

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ALEKSANDROV AI, 1995, ZH FIZ KHIM+, V69, P739

[2]

[Anonymous], 1991, Comprehensive Organic Synthesis

[3] Reaction of masked o-benzoquinones towards dienophiles with inverse electronic demand.: Enol and thioenol ethers as dienophiles [J].