A. Malpica et al., KINETICS AND MECHANISM FOR OXIME FORMATION FROM PYRIDINE-2-CARBOXALDEHYDE, PYRIDINE-3-CARBOXALDEHYDE, AND PYRIDINE-4-CARBOXALDEHYDE, Journal of organic chemistry, 59(12), 1994, pp. 3398-3401
Grime formation from pyridine-2-, -3-, and -4-carboxaldehydes occurs w
ith rate-limiting carbinolamine dehydration under both acidic and neut
ral conditions. Carbinolamine dehydration of pyridine-2-carboxaldehyde
occurs via a transition state bearing a single positive charge, unlik
e the corresponding reaction for formyl-1-methylpyridinium ion and the
reaction under acidic conditions for pyridine-3- and -4-carboxaldehyd
es.