1,4-Difluoro-2,5-dimethoxybenzene as a Precursor for Iterative Double Benzyne−Furan Diels−Alder Reactions

The use of 1,4-difluoro-2,5-dimethoxybenzene as a novel precursor for iterative two-directional
benzyne−furan Diels−Alder reactions, using a range of 2- and 3-substituted furans, is reported.
Substituted oxabenzonorbornadienes were synthesized following the initial Diels−Alder reaction,
which upon ring opening under acidic conditions gave substituted naphthol derivatives. Highly
substituted anthracenols were generated in the second benzyne−furan Diels−Alder reaction
following acid-catalyzed isomerization of the cycloadducts.