Ring closure of azo compounds to 1,2-annulated benzimidazole derivatives and further evidence of reversibility of the azo-coupling reaction | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4275970

Reference Type

Journal Article

Title

Ring closure of azo compounds to 1,2-annulated benzimidazole derivatives and further evidence of reversibility of the azo-coupling reaction

Author(s)

Del Vecchio, E; Boga, C; Forlani, L; Tozzi, S; Micheletti, G; Cino, S

Year

2015

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

2216-2222

Language

English

PMID

25615685

DOI

10.1021/jo5027244

Web of Science Id

WOS:000349943000019

URL

http://://WOS:000349943000019
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Abstract

The reaction between 1,3,5-tris(N,N-dialkylamino)benzene derivatives and 2 equiv of p-substituted benzenediazonium salts gives dicationic species which collapse to new benzimidazole derivatives with expulsion of p-substituted anilines. The presence of electron-withdrawing groups on the benzenediazo moiety of the dicationic species plays a key role in this unexpected ring closure reaction. The observed chemical behavior has been rationalized in terms of the already reported reversibility of azo coupling reactions and provided further evidence for it.