The nitrosation of imidazolines and oxazolines

Article abstract of DOI:10.1016/S0040-4039(98)00128-2

Nitrosation (HOAc / NaNO₂) of 1-methyl-2-phenyl-2-imidazoline 8 results in cleavage of only the C-N single bond and production of N- (2-methylnitrosaminoethyl)-N-nitrosobenzamide 10. In contrast, 2- phenyl-2-oxazoline 9 nitrosates very rapidly to give products (13-16) derived from a diazonium ion arising from the exclusive cleavage of the C=N.