Anthracene Derivatives as Acceptors of the Reaction Intermediate Generated by the Decomposition of Tropone Tosylhydrazone Sodium Salt. Regioselective Cycloaddition Reactions of Cycloheptatrienylidene or 1,2,4,6-Cycloheptatetraene with 9-Substituted Anthracene Derivatives

Abstract

Abstract The rearrangement of the carbene, cycloheptatrienylidene, to the allene, 1,2,4,6-cycloheptatetraene, was investigated. Tropone tosylhydrazone sodium salt, the precursor of cycloheptatrienylidene was decomposed in the presence of various kinds of 9-substituted anthracene derivatives to afford cycloaddition products, whose structures show that the carbenic carbon atom or the allenic carbon atom of the carbene or the allene attacks the carbon atoms at the 10-position of the anthracenes. It is obvious that the electronic natures of the substituents on the anthracenes have no effect on the regioselectivity of the addition reaction, suggesting that the reaction proceeds via 1,2,4,6-cycloheptatetraene, which is derived from the cycloheptatrienylidene initially generated from the tosylhydrazone.