Partially fluorinated heterocyclic compounds. Part 13. The formation of some furan derivatives from polyfluoroaryl prop-2-ynyl ethers
Abstract
Pentafluorophenyl prop-2-ynyl ether (1) undergoes isomerisation to 2-fluoromethyl-4,5,6,7-tetrafluorobenzo[b]-furan (3) on distillation in vacuo over silica at 370 °C. The ether (1) undergoes reaction with benzene and p-xylene at 140 °C to give the 2-arylmethyl-4,5,6,7-tetrafluorobenzo[b]furan derivatives (4) and (8) respectively, while 1,3,4,5,6,7,8-heptafluoro-2-naphthyl prop-2-ynyl ether (2) reacts with the same solvents at 140 °C to give the corresponding 2-arylmethyl-4,5,6,7,8,9-hexafluoronaphtho[2,1-b]furan derivatives (9) and (10) respectively.