First evidence for Wheland intermediates in azo-coupling reactions - Reactions between 1,3,5-tris(dialkylamino)benzene and arenediazonium salts

被引：22

作者：

Boga, C ^{[1
]}

Del Vecchio, E ^{[1
]}

Forlani, L ^{[1
]}

机构：

[1] Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 07期

关键词：

electrophilic substitution; aromatic substitution; diazo compounds; NMR spectroscopy;

D O I：

10.1002/ejoc.200300701

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have investigated reactions between 1,3,5-tris(1-piperidyl)benzene and 1,3,5-tris(4-morpholinyl)benzene and 4-substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are sigma complexes (Wheland-like intermediates) which are formed in almost quantitative yields and are moderately stable compounds. From these covalent complexes, products of the azo-coupling reaction may be obtained as salts or as free bases. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

引用

页码：1567 / 1571

页数：5

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