75822-19-4Relevant academic research and scientific papers
Photochemistry of N-nitroso-N-alkyl amino acids: a facile oxidative decarboxylation
Chow, Yuan L.,Horning, Douglas P.,Polo, Joel
, p. 2477 - 2483 (2007/10/02)
Several N-alkyl or N-phenyl-N-nitroso α-amino acids were synthesized and were shown to photolytically rearrange to amidoximes with concurrent decarboxylation in solution or solid states without the presence of externally added acids.In contrast, N-nitrosonipecotinic acid, a N-nitroso β-amino acid, as well as N-nitrosopiperidine in the presence of acetic acid were not photolabile.The photolability of N-nitroso α-amino acids was ascribed to the presence of an intramolecular association between the nitrosamino and carboxyl groups through hydrogen bonding.The species having the hydrogen bonding through the nitroso oxygen in the Z-configuration was believed to be photolabile and decomposed to alkylideneimines as the primary product.The mechanism of the oxidative photorearrangement was discussed.
