Download PDF
Synthesis 1994; 1994(5): 509-515
DOI: 10.1055/s-1994-25514
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.

On the Reaction of 1,3-Dichloro-2-azoniaallene Salts with Olefins and Diphenylacetylene

Martin G. Hitzler* , Clemens C. Freyhardt, Johannes C. Jochims
  • *Fakultät für Chemie der Universität Konstanz, Postfach 5560-M733, D-78434 Konstanz, Germany
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

1,3-Diaryl-1,3-dichloro-2-azoniaallene salts 1 react with di-, tri- and tetraalkyl and aryl substituted olefins to form new types of 2-azonia-allene salts 4, a 4-azapentadienyl salt 5e or pyridinium salts 8, respectively. The cycloaddition of olefins to 1,3-dichloro substituted 2-azoniaallene ions proceeds stepwise via carbocations. An X-ray structural analysis of the cycloadduct of 1 with norbornene is presented. With diphenylacetylene, compounds 1 react to give 11H-indeno[1,2-c]isoquinolinium salts 12. The free bases are generated from the hexachloroantimonates by treatment with aqueous sodium hydroxide or sodium hydrogen carbonate.