The gas phase cyclization of deprotonated N-aryl-2-diazo-2-cyanoacetamides

Abstract

Aryl-4-cyano-5-hydroxy-1,2,3-triazoles can be obtained in solution by base-catalysed cyclization of N-aryl-2-cyano-2-diazoacetamides. A similar reaction was shown to take place under conditions of negative ion chemical ionization in the ion source of a mass spectrometer. High resolution mass spectrometry, tandem mass spectrometry, charge reversal spectra, synthesis of the ions with known structures and quantum chemical calculations were used to prove the latter statement. The fact of the observed cyclization demonstrates once again the ability of mass spectrometry to study the gas phase chemical reactions that take place in solution.