It is known that $\ce{PX3 (X= Cl, Br, I)}$ and $\ce{PX5 (X= Cl, Br)}$ are used to make halogen derivatives of hydrocarbons from alcohols. My question is why there's no information about using $\ce{PF3}$? At least I couldn't find any, so I assume $\ce{PF3}$ is not used for that.

A wild guess that phosphorus holds fluorine atoms tight, and no "free" fluorides are present for the last steps of the reaction to complete.

  • $\begingroup$ related chemistry.stackexchange.com/questions/41556/… $\endgroup$
    – Mithoron
    Commented Oct 13, 2017 at 12:37
  • $\begingroup$ Yeap, I've seen that, but is this case different? $\endgroup$
    – wolphram
    Commented Oct 13, 2017 at 12:39
  • $\begingroup$ I think it's quite similar. In halogenation these halides first act as Lewis acids. $\endgroup$
    – Mithoron
    Commented Oct 13, 2017 at 12:49
  • $\begingroup$ Also a good question is whether or not fluoride is a good enough nucleophile. $\endgroup$
    – Zhe
    Commented Oct 13, 2017 at 21:44


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