REACTIONS OF PERFLUORONITRILES. II. INTERACTIONS WITH PHENYLPHOSPHINE

Article abstract of DOI:10.1016/S0022-1139(00)84963-5

Treatment of perfluoro-n-octanonitrile with phenylphosphine gave tetraphenyltetraphosphine and a spectrum of reduction and interaction products.Fifteen compounds were identified.The imine, (R_f=C7F15) R_fCH=NH, and the amine, R_fCH2NH2, were the primary reduction products.Secondary phosphorus-free products, some formed following ammonia evolution, were the following: R_fCH=NCH2R_f, R_fCH2CH(NH2)R_f, R_fC(=NH)N=CR_f(NH2), R_fCH2NHCR_f(=NH), (R_fCN)3, R_fCH=NCR_f=NCR_f(=NH), R_fCH2N=CR_fNHCH2R_f, and R_fCH2N=CR_fNHCR_f(=NH).Only three phosphorus-containing materials were definitely identified: R_fCH(NH2)P(C6H5)H, R_fCHN=CHR_f, and R_fC(=NH)P(C6H5)CR_f(=NH).Depending on reaction conditions, specific phosphorus-containing compounds could be preferentially produced.All the structure assignments are based solely on mass spectral breakdown patterns, since pure compounds were not isolated.