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Synthesis 1987; 1987(8): 745-748
DOI: 10.1055/s-1987-28073
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On the Reactions of a-Chlorocarbenium Ions with Ammonium Thiocyanate and Potassium Cyanate

Atef Hamed* , Edgar Müller, Mahmoud Al-Talib, Johannes C. Jochims
  • *Fakultät für Chemie der Universität Konstanz, Postfach 5560, D-7750 Konstanz, West Germany and Chemistry Department, Yarmouk University, Irbid, Jordan
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Publication Date:
12 September 2002 (online)

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Preparations of 1-thia-3-azabutatrienium salts 2 from ammonium thiocyanate and α-chlorocarbenium salts 3 of the Vilsmeier-Arnold type, and of the geminal diisothiocyanates 6 are described, α-Chlorocarbenium salts react with potassium cyanate and ketones or tertiary carboxamides to give 2-azaallenium salts 9. A mechanistically interesting reaction of α-chlorocarbenium cations with carbonyl compounds has been observed.