SN2 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

✍ Scribed by Rüdiger Ulbrich; Michael Famulok; Ferdinand Bosold; Gernot Boche

• Book ID: 104222123
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 254 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88855-3

✦ Synopsis

Tbe model reaction of 5 with 6 to give 7 and 8 (>90%) follows the SN~ mechankm. From this result and from product studies it is concluded that the reactions of the ultimate carcinogen 1 with 6 and deoxy8uanosine (dG) (and hence of other ultimate carcino8ens of aromatic amines with biot.mckophiles) follow the same me&a&m.

Besides of the more general interest in the nucleophilic substitution reaction at an electrophihc nitrogen center['l this reaction is of concern in relation to the carcino8enic potential of aromatic amines. What is the mechanism of the reaction of an ultimate car&o-8en of an aromatic amine, e.8 the rather labile aacetyl-N-(4_biphenyl)hy&~l~~e 1, with a bionucleophile lilte deoxy8uanosine

(dG) to give the adducts 2 and 3r21, which are also formed in viw?

4