Studies on the Voges-Proskauer Reaction. II. The Structure of a Pigment from the Diacetyl Reaction of 1-Benzyl-1-methylguanidine

A pigment formed in the diacetyl reaction of 1 -benzyl-1 -methylguanidine was isolated as reddish purple prisms. The reduced pigment was colorless and rapidly converted back to the original pigment on exposure to the air. On the basis of IR, NMR, and mass spectral evidence, the structures of the pigment and the reduced one were established to be 2-(N-benzyl-N-methylamino)-4-methyl-5-(1-oxo-1,2-dihydro-2-naphthylidenemethyl)-imidazole and 2-(N-benzyl-N-methylamino)-4-methyl-5-(1-hydroxy-2-naphthylmethyl)imidazole, respectively.

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