Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes

Article abstract of DOI:10.1139/v82-026

Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclo<4.2.0>oct-2-en-7-ols lead to tetrahydrophenanthrene derivatives.For example 8-(1-naphthyl)-bicyclo<4.2.0>oct-2-en-7-ols give substituted chrysenes in methanesulphonic acid.In the case of the homologous 7-aryl or 7,7-diarylbicyclo<3.2.0>hept-2-en-6-ols a novel transformation of diarylmethanes is observed.A mechanism is proposed which accounts for the product distribution observed in these rearrangements.