ChemInform Abstract: Chemoselective Reduction of Nitrobenzylidenemalonic Diester by an NADH Model.

ChemInform Abstract

Reduction of the p-nitrobenzylidenemalonic ester (I) is performed under two different conditions using the dihydropyridine (II) as a model compound for NADH. Reaction of (I) and (II) in the presence of magnesium perchlorate results in hydrogenation of the exocyclic double bond, yielding the benzylmalonate (III). Photosensitized reaction of (I) and (II) gives the azoxy compound (VI) probably via coupling of the nitroso derivative (IV) with the hydroxylamine (V) which are formed as intermediates. Quenching experiments show that the first step of the photochemical reaction is a one-electron transfer from eosine to (I).