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The Synthesis of Perfluoropropenyl Phosphines and Their Chemistries
[Thesis]. Manchester, UK: The University of Manchester; 2011.
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Abstract
A series of novel perfluoropropenyl-containing phosphines were prepared from the reaction of CF3CF=CFH, LDA and chlorophenyl phosphines. In this way Ph2P(CF=CFCF3) and PhP(CF=CFCF3)2 were obtained as airstable liquids, and fully characterised.Oxidation of Ph2P(CF=CFCF3) with XeF2, H2O2 and elemental selenium gave Ph2PF2(CF=CFCF3), Ph2P(O)(CF=CFCF3) and Ph2P(Se)(CF=CFCF3) respectively. For the bis-substituted compound reaction with XeF2 gave PhPF2(CF=CFCF3)2, but the reaction with H2O2 and selenium gave a mixture of products.Reaction of nBuLi or LiAlH(OtBu)3 with Ph2P(CF=CFCF3) gave Ph2P(CF=CRCF3) (R = nBu, H). The reaction of nBuLi with PhP(CF=CFCF3)2 resulted in substitution of a fluorine and as of the perfluoropropenyl groups to give PhPBu(CF=CBuCF3)2.