2
$\begingroup$

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.

$\endgroup$
4
  • $\begingroup$ 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

0

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Browse other questions tagged or ask your own question.