Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes
Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclooct-2-en-7-ols lead to tetrahydrophenanthrene derivatives.For example 8-(1-naphthyl)-bicyclooct-2-en-7-ols give substituted chrysenes in methanesulphonic acid.In the case of the homologous 7-aryl or 7,7-diarylbicyclohept-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.
Lee-Ruff, Edward,Hopkinson, Alan C.,Kazarians-Moghaddam, Hira,Gupta, Brij,Katz, Morris
p. 154 - 159
(2007/10/02)
A NOVEL ACID-CATALYZED REARRANGEMENT OF CYCLOBUTANOLS
Under acid-catalysis 7-arylbicyclohept-2-en-6-ols rearrange to diarylmethanes and cyclopenteno-annelated polycyclic aromatic hydrocarbons
Lee-Ruff, Edward,Hopkinson, Alan C.,Kazarians-Moghaddam, Hira,Duperrouzel, Paul,Gupta, Brij,Katz, Morris