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Attempted Baeyer-Villiger Reaction
| entry | oxidant | Additive | Temperature | Solvent | Result |
|---|---|---|---|---|---|
| 1 | TMSO-OTMS | SnCl4 | −20 °C | DCM | 80% PMB deprotection |
| 2 | TMSO-OTMS | CeCl3 | −20 °C to rt | DCM | No reaction |
| 3 | TMSO-OTMS | Toluene | −20 °C to rt | DCM | No reaction |
| 4 | mCPBA | TBAF | 0 °C | DCM | No reaction |
| 5 | mCPBA | None | rt | DCM | 70% epoxidation |
| 6 | Peroxyacetic acid | None | 0 °C | CHCl3 | 78% epimerization |
| 7 | Peroxytrifluoroacetic acid | None | 0 °C | CHCl3 | 62% epimerization |
| 8 | Mono peroxyphthalate (Mg salt) | None | rt | CHCl3 | 30% epimerization |
