The preparation and properties of selected annelated benzenes

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1978

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Abstract

The Diels-Alder reaction of 1,1'-dicyclopentenyl with dimethyl-1,2-cyclopentene dicarboxylic anhydride gave an adduct which upon oxidative decarboxylation provided trindan. The Diels-Alder reaction of 1-(1-cyclobutenyl)-cyclopentene with dimethyl-1,2-cyclobutene dicarboxylate gave an adduct which upon oxidative decarboxylation provided [1,2:3,4]-dicyclobuta-[5,6]-cyclopentabenzene. An analogous synthetic scheme which might lead to the preparation of the theoretically important molecule,tricyclobutabenzene,was also investigated. The preparation of para bis-norbornyl benzene was attempted by two related Diels-Alder approaches. The first involved the addition of 1,2-dimethylene-bicyclo-[2.2.1]heptane to 3,6-endo-methylene-[Delta]'-tetrahydro-o-phthalic anhydride and the second involved the addition of two moles of cyclopentadiene to one mole of p-benzoquinone. The aromatization of the ensuing adducts was not successful. Melting points, UV, 'H NMR, [raised 13]C NMR, IR, and X-ray crystallographic data were compiled for a series of known and new trisannelated benzenes.

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