Pericyclic reaction of cyclopentadienones with nonconjugated dienes. Formation of double Diels-Alder adducts.

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Abstract
Pericyclic reactions of 2, 5-bis(methoxycarbonyl)-3, 4-diphenylcyclopentadienone (Ia) with nonconjugated dienes (IIa-g) were investigated. The cyclopentadienone (Ia) reacted readily with IIa-g to give [4+2]π cycloadducts (IIIa-g) that lost carbon monoxide to afford intramolecular double Diels-Alder adducts (Va-g) on heating above the melting points. The structures of these adducts were determined from spectral evidence. The stability of the cycloadducts between twistene and isotwistene type compounds is discussed on the basis of molecular mechanics calculation data.

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