The Nef Reaction on 9,10-Dihydro-(11-nitroethano)-anthracenes. A New Route to 9,10-Dihydro-(11-ketoethano)-anthracenes

The application of the Nef reaction to the salts of the three most readily available secondary nitro 9,10-dihydro-9,10- ethanoanthracenes is reported. Two of the ketones corresponded in physical properties to samples previously prepared by other methods; the third was previously unknown. It was converted by Clemmensen reduction to a hydrocarbon, 9,10- dihydro-9,10-(11-phenylethano)-anthracene, which was synthesized independently by the Diels-Alder reaction of anthracene with styrene, thus establishing that no rearrangement had taken place during the formation of the ketone.