Nitrenium ions. Reactions of N,N-dimethyl-p-benzoyloxyanilineiminium chloride with indoles and indolizines. X-ray structure of unexpected [2-chloro-4-(4-dimethylaminophenyl-ONN-azoxy)phenylldimethylamine (azoxy derivative).
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.
Greci
Lucedio
L
Dipartimento di Scienze dei Materiali e della Terra, Università Politecnica delle Marche, Via Brecce Bianche, 1-60131 Ancona, Italy. greci@univpm.it
Castagna
Riccardo
R
Carloni
Patricia
P
Stipa
Pierluigi
P
Rizzoli
Corrado
C
Righi
Lara
L
Sgarabotto
Paolo
P