Flash vacuum pyrolysis of 2,5-diphenyloxazole

Abstract

FVP of the title oxazole (1) at 1000°C and 0.5 mm Hg afforded a complex reaction mixture containing benzonitrile, phenylacetonitrile, biphenyl, diphenylmethane, fluorene, o-benzylbenzonitrile (major product, 22%), phenanthrene, anthracene, 9,10-anthraquinone, 2-phenylindole and 3-phenylindole. A radical and carbene mechanism was suggested in order to rationalize the formation of the reaction products.