PHOSPHORUS-FLUORINE CHEMISTRY PART XLII¹. PYRROLE-SUBSTITUTED FLUOROPHOSPHORANES

Abstract

The silylated compounds, N-trimethylsilyl-pyrrole, 1, N-trimethylsilyl-2-methylpyrrole, 2, and N-trimethylsilyl-2,5-dimethylpyrrole, 3, react with the fluorophosphoranes R _n PF_5-n (n = 0,1) to give N-substituted and C-2-substituted fluorophosphoranyl-pyrrole derivatives. The preparation of the corresponding difluorophosphoranyl-pyrrole compounds was carried out by the reaction of the lithium salts of the pyrroles with diphenyltrifluorophosphorane. N-substituted phenyldifluorophosphoranyl - bis(2,5-dimethylpyrrole), 13, was obtained from the reaction of phenyltetrafluorophosphorane with the lithium salt of 2,5-dimethylpyrrole, the reaction also producing the monosubstituted phenyltrifluorophosphoranyl-pyrrole derivative, 11. The N-bonded diphenyl-difluorophosphoranyl derivatives, 10 and 12, were found to rearrange thermally to give the corresponding C-bonded derivatives, 18 and 19. The structures of the compounds are deduced from ¹H, ¹⁹F, ³¹P n.m.r. spectral data and infrared data. Mass spectral analysis was also employed for identifying the difluorophosphoranes.