Aryne chemistry. Part XXX. Approaches to the synthesis of 9-alkyl- and 9,10-dialkyl-1,2,3,4,5,6,7,8-octafluoro-9,10-dihydro-9,10-o-benzeno-anthracenes (9-alkyl- and 9,10-dialkyl-1,2,3,4,5,6,7,8-octafluorotriptycenes)

Abstract

Two routes for the preparation of 2-methyl-5-t-butylfuran have been investigated; the reactions of tetrafluoro-benzyne with this furan and with 2-methyl- and 2,5-dimethyl-furan afforded the anticipated derivatives of 1,4-epoxy-5,6,7,8-tetrafluoro-1,4-dihydronaphthalene. The methyl-substituted adducts were elaborated, with butadiene, to give 9-methyl- and 9,10-dimethyl-1,2,3,4-tetrafluoro-5,6,7,8-tetrahydroanthracenes. Further reactions with tetrafluorobenzyne, followed by dehydrogenation, afforded the title compounds.