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Chemistry

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    $\begingroup$ You are trying to get a -ve charged (or at least electron-rich) nucleophile to approach an already -ve charged molecule. Can you put a protecting group on the O- species, maybe silyl? $\endgroup$
    – Waylander
    Commented Apr 19, 2023 at 11:26
  • $\begingroup$ I see that 2 negative charges by two oxido substituents would create repulsion and is therefore energetically disfavoured. Oxiodo can be protonated to form hydroxide OH. Mechanistically I would expect that OH is attached to the molecule when F- leaves and is therefore present for a specific amount of time. Silylprotecting groups are usually cleaved by fluoride, which is a side product of the reaction. But for the next reactions I indeed plan to mask the oxido unit. $\endgroup$
    – raptorlane
    Commented Apr 19, 2023 at 11:54
  • $\begingroup$ If you have an OH group the proton is quite likely to transfer to the incoming nucleophile and inactivate it. $\endgroup$
    – Waylander
    Commented Apr 19, 2023 at 12:33