Download PDF
Synthesis 1989; 1989(12): 918-922
DOI: 10.1055/s-1989-27430
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

The Reaction of α-Chlorocarbenium Salts with Nitriles: Formation of Chloro-Substituted 2-Azoniaallene Salts

Johannes C. Jochims* , Atef Hamed, Tran Huu-Phuoc, Josef Hofmann, Helmut Fischer
  • *Fakultät Für Chemie der Universität Konstanz, Postfach 5560, D-7750 Konstanz, Federal Republic of Germany
Further Information

Publication History

Publication Date:
02 May 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Diaryl or arylchloro substituted α-chlorocarbenium salts react with benzonitriles or dimethylcyanamide to afford chloro substituted 2-azoniaallene salts 10a, b, 11c. An X-ray structural analysis confirms the constitution of one of these salts (11c). Substitution of the chlorine atoms in 1,3-dichloro-1,3-diphenyl-2-azoniaallene hexachloroantimonate (10a) by the nucleophiles water, p-cresol, p-toluidine, diethylamine, hydrazine, methyl-, phenyl-, 2.4,6-trichlorophenylhydrazine, hydroxylamine, N-phenylhydroxylamine, 1,3-dimethylurea, and ethyl allophanate have been carried out affording heterocycles and open-chain compounds 13-21.

      >