Friedel-Crafts reaction with arylcarbinols: One-pot synthesis of 10-methylbenzo[a]fluoranthene

Friedel-Crafts reaction with some monoaryl and diaryl carbinols have been s tudied. The products suggest a rational mode of formation of trityl alcohol and anthracene derivatives modifying the earlier reported conjecture of th eir formation from carbon monoxide, generated from benzyhydrol and solvent benzene. It now appears that during Friedel-Crafts reaction the benzyl carb ocation generated from benzhydrol may be arylated to triphenylmethane deriv ative. The latter under the experimental condition form, trityl cation whic h abstracts the hydroxyl group from the benzhydrol to form benzyl carbocati on and trityl alcohol. Benzyl carbocations act both as a nucleophile and an eletrophile and dimerize to form anthracene derivatives. incidentally, a o ne-pot synthesis of 10-methylbenzo[a]fluoranthene (26), characterized by NO E, decoupling and mass spectral studies, has been achieved in good yield by the Friedel-Crafts reaction of 9-fluourenol, thus providing a simple metho d of its synthesis.