S(N)2 at nitrogen: The reaction of N-(4-cyanophenyl)-O-diphenylphosphinoylhydroxylamine with N-methylaniline. A model for the reactions of ultimate carcinogens of aromatic amines with (bio)nucleophiles

Article abstract of DOI:10.1016/S0040-4039(00)88855-3

The model reaction of 5 with 6 to give 7 and 8 (≥90%) follows the S(N)2 mechanism. From this result and from product studies it is concluded that the reactions of the ultimate carcinogen 1 with 6 and deoxyguanosine (dG) (and hence of other ultimate carcinogens of aromatic amines with bionucleophiles) follow the same mechanism.