A Simple Preparation of Benzo-Fused Bicycloalkadienes from 1,3-Diene-Benzoquinone Cycloadducts

Article abstract of DOI:10.1055/s-1988-27562

Synthetic procedures are reported for the conversion of the Diels-Alder adduct of benzoquinone and both 1,3-cyclohexadiene and 1,3-cycloheptadiene to the parent hydrocarbons, 1,4-dihydro-1,4-ethanonaphthalene (benzobicyclo<2.2.2>octadiene) and 6,7,8,9-tetrahydro-5H-5,9-ethenobenzocycloheptene (benzobicyclo<3.2.2>nonadiene), respectively.The Diels-Alder adducts can be conveniently converted into the 5,8- and 1,4-dimethoxy as well as 5,8- and 1,4-diacetoxy derivatives, respectively, of these tricyclic compounds.