Reaction of Ethyl Chlorosodiocarbamate with Organic Azides

Article abstract of DOI:10.1021/jo00160a025

Ethyl chlorosodiocarbamate (3) is reactive as a nucleophile toward ethyl azidoformate (4) and tosyl azide but not toward alkyl or aryl azides.Diethyl iminodiformate (5), nitrogen gas, and sodium chloride are the principal products from the reaction of 3 with 4.Mechanistic studies support a reaction scheme involving attack of 3 at the carbonyl group of azide 4, instead of attack at the terminal azido nitrogen.The results of this study are correlated with hard and soft acid and base theory.