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Synthesis 1988; 1988(4): 332-333
DOI: 10.1055/s-1988-27562
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A Simple Preparation of Benzo-Fused Bicyclo[n.2.2]alkadienes from 1,3-Diene-Benzoquinone Cycloadducts

George H. Schmid* , Jozsef Rabai
  • *Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 1A1 Canada
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Publication Date:
20 August 2002 (online)

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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.