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Synthesis 1995; 1995(7): 820-826
DOI: 10.1055/s-1995-3995
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On the Reaction of 1,3-Dichloro-2-azoniaallene Salts with Isocyanates and Carbodiimides

Abdel-Hamid Ismail, Atef Hamed, Martin G. Hitzler, Carsten Troll, Johannes C. Jochims*
  • *Fakultät für Chemie der Universität Konstanz, Postfach 5560-733, D-78434 Konstanz, Germany
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Publication Date:
31 December 2000 (online)

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1,3-Dichloro-2-azoniaallene salts 1 react with one or two equivalents of isocyanates 2 to afford nitrilium salts 4, together with allophanoyl chlorides 5 or carbamoyl chlorides 8. The chlorides 5 and 8 were characterized by their reactions with nitrogen nucleophiles (products 10-12, 14). With antimony pentachloride, the allophanoyl chlorides 5 cyclize to 2-chloro-substituted 1,3,5-oxadiazinium salts 13. The chloro-substituted 2-azoniaallene salt 15 was obtained from the reaction of 8f with a ketone in the presence of antimony pentachloride. The 1,3-diaryl-1,3-dichloro-2-azoniaallene salt 1f adds to carbodiimides 16 to form labile 2,2-dichloro-1,3,5-triazinium salts 17, which were characterized as derivatives 18-20.

1,3-dichloro-2-azoniaallene salts - nitrilium salts - alkylideneallophanoyl chlorides - alkylidenecarbamoyl chlorides - 1,3,5-oxadiazinium salts