A dramatic solvent and stereoelectronic effect in a biomimetic oxidation: 9, 10-dialkylanthracenes

LM Tolbert, RK Khanna

Index: Tolbert, Laren M.; Khanna, Rajive K. Journal of the American Chemical Society, 1987 , vol. 109, # 11 p. 3477 - 3478

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Citation Number: 29

Abstract

7, 12-Dimethylbenz [a] anthracene (DMBA) and other alkylated aromatics undergo ring oxygenation in the presence of rat-liver microsomes containing the ubiquitous cytochrome P,,, to yield a dihydroepoxy diol.'The water-soluble fraction from the same tissue, ie, cytosol, yields not ring oxygenation but methyl hydroxylation (see Figure This diversity has been interpreted in terms of a dichotomy between direct ring oxygenation in the former case and ...