Cycloaddition reactions of 1,4-dihydronaphthalene-1,4-epoxide with cyclohexadiene and 7-(methoxycarbonyl)cycloheptatriene: Selectivity in additions

Abstract

Cycloaddition reactions of naphthalene-1,4-epoxide (1) with both 7-(methoxycarbonyl)cycloheptatriene (2) and cyclohexadiene (4) give adducts of type 3 and 5 exclusively. Selectivity was observed for the cycloaddition and bromination reactions, but neighboring group participation also occurrs in the latter. The formation of the products is discussed. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.