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Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
Shyamkanhai S Moirangthem1, Dini Ahanthem1, Sanatombi D Khongbantabam1
1Department of Chemistry, Manipur University, Canchipur, Imphal 795003, Manipur, India.
Abstract:
Dimethyl carbonimidodithioates, 2 derived from various primary aryl amines (1) by reacting with carbon disulfide and methyl iodide in dimethyl formamide in the presence of concentrated sodium hydroxide, are converted to the diaziridine derivatives, 3 by reacting with hydrazine in ethanol. The diaziridines, 3 on oxidation with lead tetraacetate in refluxing xylene, extrudes nitrogen, and intramolecular stabilization, particularly 1,2-carbon migration, takes place to give the product, 5. The reaction may take place through the intermediates, diazirines, 4, which have not been isolated. This work provides a new approach for the conversion of aryl amines having no α-methylene to aryl nitriles.
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