The dimethyl formamide – acyl halide complex and its application to the synthesis of acyl azides
DONALD E. HORNING, Joseph M. Muchowski · Canadian Journal of Chemistry · 1967
A description of the conditions which favor the formation of the acid chloride – dimethyl formamide complex is given. The utility of the complex is illustrated by its application to the synthesis of acyl azides and, in particular, by the selective formation of 3-bromopropionyl azide from the corresponding acid chloride. The complex also results from a carboxylic acid salt and N,N-dimethyl chloroformiminium chloride, and thus provides an alternative method of effecting the direct conversion of a carboxylic acid into the corresponding acid azide.