SYNTHESES AND REACTIONS OF SPIROCYCLOPROPANEANTHRONES .1. REACTIONS OF PARA-DIAZO-KETONES WITH PARA-QUINONE METHIDES

The carbenic reaction of 10-diazoanthrone (1) with 10-methyleneanthrone (2) gave dispiro[anthrone-10,1′-cyclo-propane-2′,10″-anthrone] (3), which thermally rearranged with synchronous ring expansion, yielding spiro[2H-aceanthrone-2,10′-anthrone] (7). Similar reactions of diazonaphthalen-1 (4H)-one (11) with the quinone methide (2) and of the diazo-ketone (1) with 2,6′-di-t-butyl-4-methylenecyclohexa-2,5-dien-1-one (16) afforded directly the rearrangement product, 10-hydroxytribenz[a,de,j] anthracen-5-one (12), and the cyclopropyl ring-opening product, 10-(4-hydroxy-3,5-di-t-butylbenzyl)anthrone (17), respectively, instead of the dispiro-compounds.