Diels-Alder reaction of 9-anthracenemethanol and dimethylacetylene-dicarboxy- late; potential route for the synthesis of regiospecific products of 9-substituted anthracene with unsymmetrical acetylenes

摘要

Diels-Alder reaction of 9-anthracenemethanol with dimefhylacetylene-dicarboxylate gives rise to the formation of a lactone derivative by condensation of the alcoholic function of the 9-substituent with the nearby carboxylate group in the Diels-Alder adduct. Opening of the lactone derivative with an alcohol yields the desired Diels-Alder adduct. If the alcohol used for opening the lactone is different from the alcohol part of the dicarboxylate, the reaction gives the regiospecific adduct in which the alkoxy group (used for opening the lactone) is ortho to the 9-substituent.