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Please login to access the full content or check if you have access via31.5.2.1.1 Method 1: Oxidation of Phenols with 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-Oxide
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Marsini, M. A.; Pettus, T. R. R., Science of Synthesis, (2007) 31, 405.
The oxidation of phenols to benzo-1,2-quinones with 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (1, IBX) is a mild yet powerful method for the installation of oxygen onto an aromatic ring.[1] The mechanism involves addition of the phenol to 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (1) with expulsion of water. This is followed by oxidation of the phenol to give the corresponding iodine(III) species (Scheme 1). Tautomerization, followed by further oxidation and expulsion of 2-iodobenzoic acid, gives the benzo-1,2-quinone product. Reduction of the benzo-1,2-quinone provides the desired pyrocatechol (2, benzene-1,2-diol).
Meeeee 8 Meeeeeeee ee eeeee-Meeeeeeee eeee 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-Meeee[8,8]
Meeee eeee eeeeeeeee eee eeee eeeeeeee ee eeeeeee eeeeeeee eeeeeee-8,8-eeeee eeee eee ee eeee eeeeeeeeeeeee ee eee eeeee-8,8-eeeeeee, e eeeeeeeeee eeeeee, ee eeeee eeeeee eeeeeeeeeee ee eeeee ee eee eeeeeeeeeee eeeeeeeee eeeeeeeee, eeeeeee eee eeeeeee eeeeeee-8,8-eeeee 8 eeeeeeee ee eee eeee eeee eee eeeeeeeeeee eeeeeee 8 (Meeee 8).[8]
Meeee 8 Meeeeeeee ee Meeeeee eeee 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-Meeee Meeeeee eeee Meeeeeeee ee Meeeee Meeeeeeeeee[8]
| Meeeeeeee | Meeeeeeeeeeee ee 8 (eM) | Meeeeeee ee 8 (eeeee) | Meeeeee | Meee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|
 |
88 | 8.8 | MMMe8/MeMM (8:8) | 88 eee | |
88 | [8] |
| |
888 | 8.8 | MMMe8 | 88 e | |
88 | [8] |
| |
88 | 8.8 | MMMe8/MeMM (8:8) | 88 e | |
88 | [8] |
| |
88 | 8.8 | MMMe8 | 88 e | |
88 | [8] |
| |
88 | 8.8 | MMMe8 | 88 e | |
88 | [8] |
| |
88 | 8.8 | MMMe8/MeMM (8:8) | 8 e | |
88 | [8] |
8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee (8) eee eeee eeee eeee eee eee eeeeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeee 8-(8,8-eeeeeeeeeeeeeee)-8,8-eeeeeeeee-8,8-eeeeeee-8M-8-eeeeeeeeee-8-eee (8, eeeeeeeeeee) eeee eeeeee eeeeeeeee 8. Me e eeeeeee eeeeeee, eeee 8 ee eeeeeeee eeee eeeeee eeeeeeeeee 8 ee eee eeeeeeeee ee (8eM,88eM)-8,88e-eeeeeeeeeee[e]eeeeee[8,8-e]eeeee-8,8e,8,88(8M)-eeeeee [8, (±)-eeeeeeeee] (Meeeee 8).[8,8] Meeeeeeee ee eee eeeeeeeeeeee eeeee-8,8-eeeeeee ee eeeeeeeeeeee ee eeee eeee eeeeee eeeeeeeeee (Me8M8M8) ee eeee eee eeeeeee eeeeeee-8,8-eeee.
Meeeee 8 Meeeeeeee ee Meeeeee Meeeeeee eeee 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-Meeee[8,8]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee Meeeeee-8,8-eeeee 8; Meeeeee Meeeeeeee:[8]
MMMMMMM: MMM ee eeeee ee eeeeeee eeee eeeeee eee/ee ee eeee eeeeeeeeeee.
Me e eeeeeee eeee ee e eeeeee 8 (8.88 eeee) ee MMMe8/MeMM (8:8 e/e; 88 eM) ee −88°M eee eeeee MMM (8; 8.88 eeee). Meee eeeeeeee ee eee eeeeeee, eee eeee eeeeee eeeeee-eeeeee, eee eee eeee eeeeeee eee 88 e. MeMM8 ee MeMM (88 ee·eM−8) eee eeee eeeee, eeee eeeeeeee eeeeeeee ee −88°M, eeeee eeee eeee ee eee eeeeee-eeeeee eeeee ee eee eeee eeeeeeeeeee (eeeeeee eeeeee 8 eee). Meeeee MeMM8 eee eeeeeee ee eeee eeeeeeeeeeeee eeee MeMM (8.8–8.8 eM) eee eee eeeeeee eee eeeeee eeee eee. eeeee eeeeeeeeee 88% Me8M8M8, eeeeeeee ee eM 8 eeee Me8MM8 (8 × 88 eM). Mee eeeeeee eeeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeee MMM [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)/MeMMe/MeMM 8:8:8.88]; eeeee: 88–88%.
8-(8,8-Meeeeeeeeeeeeee)-8,8-eeeeeeeee-8,8-eeeeeee-8M-8-eeeeeeeeee-8-eee (8, Meeeeeeeeee):[8]
MMMMMMM: MMM ee eeeee ee eeeeeee eeee eeeeee eee/ee ee eeee eeeeeeeeeee.
Me e eeee ee eeeee 8 (8.888 e, 8.88 eeee) ee MMMM (888 eM) eee eeeee MMM (8; 8.888 e, 8.88 eeee), eee eee eeeeeee eee eeeeeee ee ee eee 8 e. Me eee eeeeeeee eeeeeeeeee, e eeeee eeeeee eee eeeeeeee ee eee eeee eeee eeeeeeeeeee eeeeee ee eeeeee eeeee. Me8M8M8 (8.88 e, 88.8 eeee) eee eeeee, eee eee eeee eee eeeeeee eee ee eeeeeeeeee 8 e. Mee eeeeeeee eee eeeeeeee eeee M8M (888 eM) eee eeeeeeeee eeee MeMMe (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeeee (eM 8.8), M8M, eee eeeee, eee eeee eeeee (MeMM8), eeeeeeeeeeee, eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8); eeeee: 8.888 e (88%).
8-[(Meeeeeeee)eeeeee]-8,8-eeeeeee-8M-eeeeee-8,8,8-eeeee (8); Meeeeee Meeeeeeee:[8]
MMMMMMM: MMM ee eeeee ee eeeeeee eeee eeeeee eee/ee ee eeee eeeeeeeeeee.
Meee 8 (88 ee, 8.888 eeee) ee MMM (8 eM) eee eeeeeee eeee MMM (8; 88.8 ee, 8.888 eeee) ee ee. Meeee 8 e, Me8M8M8 (88.8 ee, 8.88 eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee ee eeeeeeeeee 8 e eeeeee eeeee eeeeeeee eeee 8 M MM8Me, eeeeeeeee eeee Me8M, eeeeee eeee eeeee eee M8M, eeeee (MeMM8), eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8); eeeee: 88.8 ee (88%).
References
| [1] | Meeeeeee, M.; Meeeeeeee, M. M.; Mee Me Meeee, M. M.; Meeeee, M. M. M., Mee. Meee., (8888) 8, 888. |
| [2] | Meeeeeee, M.; Meeee, M.; Meeeeeeeee, M.; e'Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [3] | Meeeeeee, M.; Meeeee, M. M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [4] | Meeee, M.; Meeee, M.; Meeeee, M. M. M., Mee. Meee., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
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