Base-catalyzed decomposition of N-nitrosobis(2-oxopropyl)amine.
N-Nitrosobis(2-oxopropyl)amine, a potent carcinogen for the pancreas in Syrian hamsters, undergoes a facile, base-catalyzed, intramolecular aldol condensation to yield N-nitroso-5-hydroxy-5-methyl-3-piperidone. This cyclic nitrosamine then decomposes to yield 3-hydroxy-5-methylpyridine.
Boux
L J
LJ
Department of Medical Biophysics, University of Toronto, Ontario, Canada.
Milligan
J R
JR
Archer
M C
MC
D002273:Carcinogens / Q000737:chemistry*; D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008968:Molecular Conformation; D009602:Nitrosamines / Q000737:chemistry*; D013237:Stereoisomerism
D002273:Carcinogens; D009602:Nitrosamines; C013622:nitrosobis(2-oxopropyl)amine