4561-35-7Relevant articles and documents
Rearrangement of Carboxylates derived from N-Acetyl-N-nitroso-&α-amino-acids
Chow, Yuan L.,Polo, Joel
, p. 297 - 299 (1981)
While N-acetyl-N-nitrosophenylalanine thermally decomposes by the known mechanism, its carboxylate anion undergoes facile rearrangements initiated by carboxylate attack in methanol or water to give 2-methoxy- or 2-hydroxy-3-phenylpropanoic acid, respectively.
THE PHOTOELIMINATION OF N-NITROSO-N-ACETYL-α-AMINO-ACIDS; A NEW SYNTHESIS OF 1,2,4-OXADIAZOLES
Chow, Yuan L.,Polo, Joel S.
, p. 727 - 734 (2007/10/02)
The excitation of N-nitroso-N-acetyl-α-aminoacids, nitrosopeptide model compounds, under neutral and weakly basic conditions, caused the homolysis of the N-N bond followed by decarboxylation to give hyponitrous acid (HNO) and N-acetylimines which were susceptible to nucleophilic addition.While weak bases caused the carboxylate group to assist intramolecular rearrangement to a small extent, they functioned primarily to provide nucleophilic NO-, which initiated nucleophilic attack leading to the C-nitroso derivatives.These C-nitroso derivatives spontaneously cyclized to 1,2,4-oxadiazoles much more rapidly than tautomerism to the corresponding oximes; the latter oximes failed to cyclize under the basic conditions.
