A previous report [1] has identified a novel regioselective oxidation of 1,2,3,6-tetrahydr~,yridines having a phenyl group in the 4 position. In this work we have studied the oxidation of the tetrahydropyridine I which has a 3,-pyridyl substituent at C 4. Through its conjugation with the allylamine part of the piperidine ring, this heteroaromatic r-defuzient substituent can affect the reactivity in two ways. Firstly, it can activate oxidation of the C 7 methyle~ group to a ketone and secondly ...