A number of arynes, generated by treatment of haloarenes with sodium or potassium amide
in tetrahydrofuran, were trapped with furan. The resulting dihydro epoxy arenes were
converted into the following annulated isobenzofuran derivatives by using reverse Diels-Alder
methodology: naphtho[l,2-clfuran, phenanthro[9,10-elfuran, pyreno[l,2-elfuran, pyreno[3,4-
elfuran, anthra[l,2- elfuran, phenanthro[l,2- clfuran and phenanthro[3,4- elfuran. Bimolecular
rate constants for the addition of maleic anhydride to these furans were measured, and were
correlated with the Herndon structure count. Addition of arynes to selected members of this furan
series yielded adducts which were deoxygenated to afford polycyclic aromatic hydrocarbons.
A number of arynes, generated by treatment of haloarenes such as (I) with NaNH2 or KNH2 are trapped with furans (II) to give dihydroepoxy arenes such as (III).
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