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A mutant strain of Beijerinckia, after growth with succinate plus biphenyl, contains an enzyme system that oxidizes benzo [a] pyrene and benzo [a] anthracene to mixtures of vicinal dihydrodiols. The major dihydrodiol formed from benzo [a] pyrene was identified as cis-9, 10-dihydroxy-9, 10-dihydrobenzo [a] pyrene by comparison with a synthetic sample. Benzo [a] anthracene was metabolized to four dihydrodiols, the major isomer being cis-1, 2-dihydroxy-1, 2-dihydroxy-1, 2-dihydrobenzo [a] anthracene.

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A solution of 1 (105 mg, 0.99 mmol) in carbon tetrachloride (2 mL) was added under argon to a solution of freshly sublimed tetracyanoethylene (127 mg, 0.99 mmol) in the same solvent (2 mL) at room temperature. Initially, a bright mauve color was observed. After being stirred for 2 days, the reaction mixture was filtered through a bed of Celite, which was rinsed with carbon tetrachloride. Evaporation of the filtrate provided 63 mg (27%) of 14 as a white crystalline solid. Following recrystallization from chloroform and sublimation (90 °C and 0.05 torr), the adduct exhibited a decomposition point of 182 °C: