Abstract
The absolute stereochemistry of a series of 3-substituted cis-dihydrodiols obtained by microbial oxidation of toluene, ethylbenzene, chlorobenzene, and biphenyl has been assigned from chemical and spectrophotometric studies. ϱ-Halogenated toluenes also have been investigated as substrates in these oxidations, and the corresponding cis-dihydrodiols isolated. Implications from the observation that some of the cis-dihydrodiols are racemic are discussed. Oxidation of an olefin, (±)-3-methylcyclohexene, by these microorganisms leads only to cis-diols whose absolute stereochemistry about the hydroxyl-bearing carbons is the same as that found for the cis-dihydrodiols formed from the aromatic substrates.
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