Diels-Alder reaction of tetraarylcyclopentadienones with benzo[]thiophene ,-dioxides: an unprecedented de-oxygenation sulfur dioxide extrusion

Diels-Alder reaction of tetraarylcyclopentadienones with benzo[ b ]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence of aryl substituents present on cyclopentadienones. The intermediate dihydrodibenzothiophene-dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes or benzenes. The Diels-Alder adduct, dihydrodibenzothiophene S , S -dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes or benzenes.