The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-nitro- and 11-amino-9,10-Dihydro-9,10-Ethanoanthracenes

The preparation of a series of seven Diels-Alder adducts of anthracene and common nitroolefins unsubstituted, 1- or 2- monosubstituted or 1,2- or 2,2-disubstituted is described; in the latter two cases the practical limits of the reaction appear to have been reached. The four adducts obtained in the best yields (19-62%) have been converted to the corresponding amines and their derivatives. The ultraviolet spectra of all the compounds compare favorably with the spectra of dihydroanthracenes reported in the literature.