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-methyln
itrosaminoethyl)-N-nitrosobenzamide 10. In contrast, 2-phenyl-2-oxazol
ine 9 nitrosates very rapidly to give products (13-16) derived from a
diazonium ion arising from the exclusive cleavage of the C=N. (C) 1998
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