Issue 21, 2003
From the journal:

Organic & Biomolecular Chemistry

Nitrenium ions.† Reactions of N,N-dimethyl-p-benzoyloxyaniline-iminium chloride with indoles and indolizines. X-ray structure of unexpected [2-chloro-4-(4-dimethylaminophenyl-ONN-azoxy)phenyl]dimethylamine (azoxy derivative)

Lucedio Greci,*a   Riccardo Castagna,a   Patricia Carloni,a   Pierluigi Stipa,a   Corrado Rizzoli,b   Lara Righib  and  Paolo Sgarabottob  

* Corresponding authors

a Dipartimento di Scienze dei Materiali e della Terra, Università Politecnica delle Marche, Via Brecce Bianche, I-60131 Ancona, Italy
E-mail: greci@univpm.it

b Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università di Parma, Viale delle Scienze, I-43100 Parma, Italy

Abstract

N,N-Dimethyl-p-nitrosoaniline reacts with benzoyl chloride affording a complex salt containing a cation, a hybrid between a nitrenium ion and an iminium ion. The salt reacts with nucleophiles (indoles, indolizines) yielding compounds characterized by a new carbon–nitrogen bond, derived from the nitrenium ion form. According to the type of nucleophile, the reaction, to differing extents, is in competition with an electron transfer process which leads to the formation of the dimer of the nucleophile and of the azoxy corresponding to the N,N-dimethyl-p-nitrosoaniline. In one of the reactions studied, a chlorinated azoxy derivative was also isolated, and its structure was elucidated by X-ray analysis.

Graphical abstract: Nitrenium ions. Reactions of N,N-dimethyl-p-benzoyloxyaniline-iminium chloride with indoles and indolizines. X-ray structure of unexpected [2-chloro-4-(4-dimethylaminophenyl-ONN-azoxy)phenyl]dimethylamine (azoxy derivative)

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Article information

DOI
https://doi.org/10.1039/B308088A
Article type
Paper
Submitted
17 Jul 2003
Accepted
08 Sep 2003
First published
01 Oct 2003

Org. Biomol. Chem., 2003,1, 3768-3771

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Nitrenium ions. Reactions of N,N-dimethyl-p-benzoyloxyaniline-iminium chloride with indoles and indolizines. X-ray structure of unexpected [2-chloro-4-(4-dimethylaminophenyl-ONN-azoxy)phenyl]dimethylamine (azoxy derivative)

L. Greci, R. Castagna, P. Carloni, P. Stipa, C. Rizzoli, L. Righi and P. Sgarabotto, Org. Biomol. Chem., 2003, 1, 3768 DOI: 10.1039/B308088A

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