Reactivities of dianions of pyridyl phenyl ketones

Abstract

Substituted pyridylphenylcarbinols are formed in the reaction of the dianions of isomeric pyridyl phenyl ketones with alkyl halides, aldehydes, and benzonitrile. The reaction of the dianion of 3-pyridyl phenyl ketone with benzophenone, in contrast to the analogous reaction of the dianion of 2-pyridyl phenyl ketone, gives 5-benzoyl-2-diphenylhydroxymethyl-1,2-dihydropyridine. It is assumed that the observed reaction includes one-electron transfer and the formation of two anion radicals. Recombination of the anion radical of 3-pyridyl phenyl ketone leads to 5,5′-dibenzoyl-2,2′-di(1,2-dihydropyridyl).