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Please login to access the full content or check if you have access via37.2.1.4.1 Method 1: Manganese-Mediated Epoxidation with Hydrogen Peroxide
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Adolfsson, H., Science of Synthesis, (2008) 37, 248.
The introduction of chlorinated porphyrin 18 allows for hydrogen peroxide to be used as terminal oxidant.[78] This catalyst has been demonstrated to resist decomposition, and, when used together with imidazole or imidazolium carboxylates as additives, efficient epoxidation of alkenes is achieved (Table 4, entries 1, 2).
Meeee 8 Meeeeeeee–Meeeeeeee Meeeeeeee Meeeeeeeeee ee Meeeeeeeeee Meeee 88% Meeeeee Meeeeeee Meeeeeee[88,88]
Meeee | Meeeeeee | Meeeeeee | Meee (°M) | Meee (eee) | Meeee (%) | Mee |
---|---|---|---|---|---|---|
8 | 8.8 eee% 88 | eeeeeeeee (8.8 eeeee) | 88 | 88 | 88 | [88] |
8 | 8.8 eee% 88 | 8.8 eee% M-eeeeeeeeeeeeee, 8.8 eee% MeMM8M | 8 | 88 | 888 | [88] |
8 | 8.8 eee% 88 | – | 8 | 8 | 888 | [88] |
Mee eeeeeeeeeee eeee eeeeeeeeee eee eeeeeeeeee eeeee eeeeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeeeeee eee eee ee eee eeeeeeeeeee ee eeeeeeeee–eeeeeeeee eeeeeeeee eeee ee 88 eeeeeeeeee eeeee eeeeee eeeeeeeeee eeeeee ee eee eeeeeeeee eeeeeeee ee eeeeeee eeee.[88] Meee eeeee eeeeeeeee eee eeeeeeee ee eee eeeeeeeeeee ee eeeeee eeeeeee eeee eeeeeeee eeeeeeee, eeeeeeee eeeeeeeee eeeee ee eeeeeeeeeee eeee eeeeeee eeeeeee eeeeeeeeeee ee eeeeeeee (Meeee 8, eeeee 8). Me eeeeeeee ee eeeeeeeeeeee eeeeeeeee ee eeeee eeeeee, eee eeeeeeeee–eeeeeeeee eeeeee eeeeee eeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeee. Mee eeeeeee, eee eeeeeeeeeee ee M-eeeeeeee eeeee (8,88,88,88-eeeeeeeeeeeeeeeeeeeeeee)eeeeeeeee(MMM) eeeeeeee eee eeeeeeeeeeeeee, eeeeeeeee eee- eee eeeee-8,8-eeeeeeeeeeeeeee ee e eeeee ee 8:88. Mee eee eeeeeeeeeeeeeeeee ee eeeeeeee eeeee eeeeeeeeeeee eeeeeeeee eeee ee eeeeeeeee ee eeeeeeeeee. Mee eeeeeeeeeee eeeeee eeeee eeeeeeee eeeeeeee ee eeeeeeee eeeeeee ee eeeeeeee ee ee eeeeeeeeeeeeee eee M-eeeeeee, eeeeeee M-eeeeeee eee eeee eeeeeeeeee eeee eeeee eeeeeeeee.
Meeee eeee eeeeeeeee-eeeee eeeeeeeee, eeeeeeeee eeeeeeeee ee M-eeeeeeeee 8,8,8-eeeeeeeeeeeeeeeee 88 (MMMMMM) (Meeeee 88) eeee eeee eeeee ee eeeeeeeeeee eeeeeeee eee eeeeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeee eeeeeeeee (eeeeeeeee eeeeee, eeeeeeee, ee eeeeeee eeee) eee eeeeeeee eeeeeeee.[88–88] Meeeeeeee eeeeeeeee eeeeeee eeee eeeeeeee e eeee eeeeee (ee 888 eeeee) ee eeeeeeee eeeeeeee eee eeeeeeeee eeeeeeeeeee. Mee eeeeee eeeeeeeee eeeeeeeeeee ee eee 8,8,8-eeeeeeeeeeeeeeeee eeeeeee eee eee ee ee eeeeeeeee eeeeee ee eeee eeeeeeeeeee eeeeeee eeee eeeeeee eeeeeeeeeeee eeeeeeeeee. Me eeee eeeeeee, eeeeeee–eeeee eeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeeeeeee. Meeeeee eee eeeeeeeee eeee eeeee eeee eee eeeeeeeee eeeeeeeee eeeeeee 88, eeeeeeee eeee eee eeeeeeeeeeee eeeeee 88, ee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeeee ee eeeeee eeeeeee.[88] Meee 8.8 eee% ee eeeeeeee 88 ee eeeeeeee eee eeee eeeeeeeeee (88%) ee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee. Me eeeeee ee eeeeeee eeeeeeee eeeeeeee (8 eeeee) ee eeee eee ee eee eeeee eeeeeee ee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee.
Meeeee 88 Meeee Meeeeee[88]
Me e eeeeeeeee ee eeeeeeeee eeeee eeeee, eeeeee eeeeeeeee(MM) eee eeeeeeeee(MMM) eeeee eee eeeee ee eeeeeeee eee eeeeeeeee ee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeee-eeeee eeeeeee eeeee eeeeeee eeeeeeee eeeeeeee (Meeeee 88).[88] Me eee eeeeeee eeee eeeeeeeeeee eeee eee eeeeeeee ee eeeeeeeeeee ee ee eeeeeeeeee eee eee eeeeeeeeeee eeeeeeee.
Meeeee 88 Meeeeeeee(MM) Meeeeee Meeeeeeee Meeeeeeeeee ee Meeeeee Meeee Meeeeee Meeeeeee Meeeeeee[88]
M8 | M8 | M8 | M8 | Me Meeeeeee | Meeeeeeee Meee (8 eee%) | Mee | M8M8 (eeeee) | Meeee (%) | M8M8 (eeeee) | Meeee (%) |
---|---|---|---|---|---|---|---|---|
(MM8)8 | M | M | 88 | 88 | 8.8 | 88 | [88] | |
M | M | 88 | 88 | 8 | 88e | [88] | ||
Me | M | Me | M | 88 | 88 | 8 | 88e | [88] |
(MM8)8 | Me | M | 88 | 88 | 8 | 88e | [88] | |
Me | M | M | Me | 88 | 88 | 88 | 88 | [88] |
Me | Me | M | M | 88 | 88 | 88 | 88 | [88] |
(MM8)8Me | M | M | M | 88 | 8 | 88 | 8 | [88] |
e Meeeeeee eeeeee.
Meeee eeeeeeeeeeeee eeeeeee, ee eee eeee eeeeeeeeeee eeee eeeeeeeeeeeeeeeeeee (MMM8−) ee eeeeee eeee eeeeee eeeeeeee eeeeeeee eee eeeeeeeeeee.[88] Me eee eeeeeee ee eee eeeee eeeeeeee, eee eeeeeeeee eeeee ee eee ee eeee eeeeee eeeeeeeeeeeeeeeeeee, eeee eeeeeee ee eee eeeeeeee eeee eeeeeee, eee eeee eeeeeeeeeeee ee ee eeeeeeee. Me eee eeeeeee eeeeeeee eeeee, eeee eeeeeeeee(MM) eeeeeee eeeeeeeee eeeeeeeeeee eeeeeeee e eeeeeeeeeeee eeeeee ee eeeeeeee eeeeeeee (88 eeeee) eee eeeeeeeee eeeeeee eeeeeeeee. Meeeeeeee eee eeeee ee eee eeeeeeee, ee eee eeee eeeee eeee eeeeeeee-eeee eeeeeeeeee eeee ee ee-, eee-, eee eeeeeeeeeeeeeeee eeeeeee eeee eeeeeeee ee eeee eeeeee ee eeeee eeeeeeeeeeeee eeeeeeee. Meeeeeeeeeee eee eee eeeeeeeeeee eeee eeeee eeeeeeee, eeeeeee eeeeeeeee-eeeeeeeeeee eeeeeeeeee eee eeeeeeeeee eeeeeeeeee eeeee eeeee eeeeeeeeee. Mee eeeee eeeeeeee eeeeee eeee ee eeee eeeeeeeeee eee eeeeeee eeeeeeeeee; eeeee, eeee-eeeeeeeee eeeeeeee eee eeeeee ee eeee eeeeee. Meeeeeeee eeeeeeeee eeee eeee eeeeeeee ee eeeeeee eeee eeeeeeeeeee eeeeee, eee ee eee eeee eeeee eeee eee eeeeeeee ee eeeeee eeeeeee ee eeeeeeeeee eee eeeeeeeee eeeeeeeee ee eeee-eeeee eeeeeee. Meeeeeeee, eee eeeeeeee ee eeeeeeeee eeee eeeeeeee eee eeeeeee ee eee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeee. Mee eee ee eeeee eeeeeeeee eeeeeeeeeee eeeeeee eee eeeeee ee eeeeeeee eeeeeeee eeeeeeeeeee eeeeeeeee eee e eeeeeeeeee eeeeeeeeeee (Meeeee 88). Mee eeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeee ee M-eee-8-eee eeeeee e eee/eeeee eeeeeee ee eee eeeeeee (8:8.88 eeeeeee eeeeeeee eee 8:8.8 ee eee eeeeeeee ee 8 eee% eeeeeeeee eeee).
Mee eee ee eee eeeee eeeeee 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee [(eeee)MM8] eeeeeee eeeeeeee eee Meeeeee eeeeeeeeeee eeeeee.[88] Meeeeeeee eeeeee eeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeeee, eee eeeeeeeeee eee eeeeeeee ee 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee, eeeeee eee eeeeeeeee eeeeeeeeeee ee e eeeeee ee eeeeeeeee eeeeeee, eeeeeeeee eeeeeeeeee eeeeeee ee eeee-eeeeee eeeeeeee, e.e. eeeeeeeeeeeeeeeeee (88% eeeee) eee 8-eeeeeeeeeeeeeeeee (88% eeeee).
References
[78] | Meeeeeee, M.; Meeeee, M.-M.; Meeeeee, M. M.; Meeee-Meeeeee, M.; Meee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[79] | Meeeee, M. M.; Meeee, M.; Meeeeeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[80] | Meee, M.; Meeee, M. M.; Meeeeeeee, M.; Meee, M. M.; Meeeeee, M. M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M.; eee Meeee, M. M. M.; Meeeeee, M. M.; eee eee Meee, M.; Meeeeee, M., Meeeee (Meeeee), (8888) 888, 888. |
[81] | Me Mee, M. M.; Meee, M. M.; Meeeeeee, M.; Mee, M. M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[82] | Meeeeeeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[83] | Meeeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 888. |
[84] | Meee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[85] | Meee, M. M.; Meee, M.; MeMeee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
[86] | Meee, M.-M.; Meee, M.-M.; Meee, M. M., Mee. Meee., (8888) 8, 8888. |