4669-85-6Relevant articles and documents
Reactive E=C(p-p)?-Systems, VI. Reactions of the Phosphaalkene F3CP=CF2 with H Acidic Compounds
Grobe, Joseph,Van, Duc Le,Nientiedt, Juergen
, p. 149 - 161 (2007/10/02)
The reactions of the perfluorophosphaalkene F3CP=CF2 (1) with HX compounds proceed via addition to the PC double bond yielding either secondary phosphanes F3CP(H)CF2X (X = OH, OR, NR2, PMe2) or PX derivatives F3CP(X)CF2H (X = Cl, Br, SMe, SeMe, AsMe2).The rate of reaction with H2O is strongly pH-dependent, but only at pH > 13 the opposite direction of addition is observed.Similar results are obtained for the addition of alcohols, for which the presence of OR(-) results in two effects: (i) Reversion of the addition direction to yield F3CP(OR)CF2H; (ii) HF elimination from F3CP(H)CF2OR to give substituted phosphaalkenes.With strong bases HNR2, the addition is followed immediately by HF elimination producing the surprisingly stable phosphaalkenes F3CP=C(F)NH2 (R = Me, Et).Secondary phosphanes of the type F3CP(H)CF2X (X = OMe, OEt, PMe2) are found to be suitable precursors for the preparation of novel heterosubstituted derivatives of 1 by elimination of HF with NMe3.New compounds were characterized by NMR, MS, GC/MS and GC/IR measurements. - Keywords: HX Addition to F3CP=CF2, New Chiral CF3 Substituted Phosphanes, Phosphaalkenes, Mass Spectra, NMR Spectra
