Chemistry Letters, Vol.44, No.7, 967-969, 2015
Thermal Reaction of 4-(p-Aminopheny1)-1-sulfonyl-1,2,3-triazoles Furnishing Benzoyl Cyanides through N-Sulfinyl Imine Intermediates
A thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles forming benzoyl cyanides is reported. A carbene species thermally generated from the triazole by denitrogenation undergoes intramolecular oxygen migration from sulfur to carbon, giving an N-sulfinyl benzoylimine intermediate. The subsequent Cope-type elimination of the sulfinyl group gives rise to cyano functionality.