Ortho-Disubstituted F-Benzenes. IV. The Formation of 2-Acyl-F-phenyl Carboxylates from (F-Benzo)furans by the Oxidative Cleavage of the Furan-ring

Abstract

Abstract 2,3-Diphenyl-, 2-phenyl-3-methyl-, and 2-methyl-3-phenyl(F-benzo)furans were oxidized with chromium trioxide in acetic acid to yield 2-benzoyl-F-phenyl benzoate, 2-acetyl-F-phenyl benzoate, and 2-benzoyl-F-phenyl acetate respectively, while 2-phenyl(F-benzo)furan was least susceptible to the same reagent, affording 1-(2-hydroxy-F-phenyl)-2-phenylethanedione in a poor yield. The spectral data of the products were compatible with the structure of ortho-disubstituted F-benzene.