N-Monochlorination and N-monobromomination of carbamates and carboxamides by sodium hypochlorite and hypobromite

C. Bachand , H. Driguez (1) , J.M. Paton , D. Touchard (2) , J. Lessard

1 CERMAV - Centre de Recherches sur les Macromolécules Végétales
2 UdeS - Département de chimie [Sherbrooke]

Our studies on the chromous chloride promoted addition of N-chlorocarbamates to olefins led us to devise a convenient method for the preparation of N-monochlorocarbamates in high yield, free from the N,N-dichloro derivatives. This method was also applied to the preparation of N- monochlorocarboxamides and of N-monobromocarbamates and -carboxamides needed for the chromous chloride promoted addition studies and some photochemical work. The recent publication of Swern and coworkers on the preparation of ethyl and methyl N-chlorocarbamates prompted us to report our results.

Domaines: Polymères; Chimie organique

C. Bachand, H. Driguez, J.M. Paton, D. Touchard, J. Lessard. N-Monochlorination and N-monobromomination of carbamates and carboxamides by sodium hypochlorite and hypobromite. Journal of Organic Chemistry, 1974, pp.3136-3138. ⟨hal-00307101⟩