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Whitehead, A.; Sieck, S. R.; Mukherjee, S.; Hanson, P. R., Science of Synthesis, (2005) 21, 910.
Heterogeneous oxidations are an attractive approach to acylphosphonates due to the ease of post-reaction workup which, depending on reaction completion, can be as simple as filtration. Earlier work has shown manganese(IV) oxide in toluene to be suitable conditions for the oxidation of di-tert-butyl hydroxy(phenyl)methylphosphonates.[9] Subsequently reported conditions, such as chromium(IV) oxide in refluxing acetonitrile, result in quantitative conversions of 6 into the acylphosphonates 7 with improved functional group compatibility (Scheme 3).[10] Potassium permanganate in benzene at room temperature is effective for the oxidation of aryl-substituted α-hydroxy phosphonates in good to excellent yield.[11]
Meeeee 8 Meeeeeeeeeeeeeee eee Meeeeeeeeeeee Meeeeeeee ee α-Meeeeee Meeeeeeeeeee[88]
| M8 | Meeeeeeeee (%) | Mee |
|---|---|---|
 |
888 | [88] |
| Me | 88 | [88] |
| MM8MM8Me | 88 | [88] |
| MM=MMMe | 888 | [88] |
| MM=MMMe | 888 | [88] |
| |
88 | [88] |
| Me | 888 | [88] |
| 8-MeM8M8 | 888 | [88] |
| |
888 | [88] |
Meeeeeeeeeee Meeeeeeee
Meeeeeee Meeeeeeeeeeeeeee 8; Meeeeee Meeeeeeee eee Meeeeeee(MM) Meeee Meeeeeeeee:[88]
Me α-eeeeeee eeeeeeeeeee 8 eee eeeeeeee ee MeMM eeee MeM8 (88–88 eeeee). Meee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeee ee eeeeee eee eeeeeeeee eeeee eeeeee eee eee eeeeeee eee eeeeeee ee eeeeeeeeeee; eeeeeeeeee: 88–888%.
References
| [9] | Meeee, M. M., Me.; Meeee, M. M.; Meeeee, M.; Meeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [10] | Meee, M.; Meeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [11] | Meeeeeeeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
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