Timeline for Improve the leaving capability of a leaving group (F-) with electron density donating groups (EDP) in close proximity (neighboring group effect)?
Current License: CC BY-SA 4.0
8 events
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| Apr 19, 2023 at 12:33 | comment | added | Waylander | If you have an OH group the proton is quite likely to transfer to the incoming nucleophile and inactivate it. | |
| Apr 19, 2023 at 11:54 | comment | added | raptorlane | 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. | |
| Apr 19, 2023 at 11:26 | comment | added | Waylander | 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? | |
| Apr 19, 2023 at 11:15 | history | edited | raptorlane | CC BY-SA 4.0 |
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| Apr 19, 2023 at 11:11 | history | edited | raptorlane | CC BY-SA 4.0 |
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| Apr 19, 2023 at 11:10 | history | edited | raptorlane | CC BY-SA 4.0 |
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| S Apr 19, 2023 at 11:08 | review | First questions | |||
| Apr 19, 2023 at 14:29 | |||||
| S Apr 19, 2023 at 11:08 | history | asked | raptorlane | CC BY-SA 4.0 |