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Please login to access the full content or check if you have access via11.12.1.1.2.6 Method 6: By Oxidative Addition of α-Methylene Ketones to Nitriles
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Boyd, G. V., Science of Synthesis, (2002) 11, 395.
α-Methylene ketones react with iron(III) solvates of nitriles R1CN to give oxazoles 1 (Scheme 22).[53]
Meeeee 88 Meeeeeee eeee Meeeeeeee Meeeeeee ee α-Meeeeeeee Meeeeee ee Meeeeeee[88]
M8 | M8 | M8 | Meeeeee | Meee (eee) | Meeee (%) | Mee |
---|---|---|---|---|---|---|
Me | M | Me | M | 88 | 88 | [88] |
Me | Me | Me | M | 88 | 88 | [88] |
MM8MM8MM | Me | Me | M | 888 | 88 | [88] |
MM8MM8MM8Me | Me | Me | M | 888 | 88 | [88] |
Me | Me | Me | M | 888 | 88 | [88] |
MM8MM8Me | Me | Me | M | 88 | 88 | [88] |
MM8MM8MM8M | Me | Me | M | 88 | 88 | [88] |
MM8MM8M | Me | Me | M | 8 | 88 | [88] |
MM8MM8M | Me | Me | M | 88 | 88 | [88] |
MM8MM8MM8M | Me | Me | M | 88 | 88 | [88] |
e Mee eeeeeeeeeeee eeeeeeeeee eee eeeeeee.
Meeeeeeeeeee Meeeeeeee
Meeeeeee 8 ee Meeeeeeee Meeeeeee ee α-Meeeeeeee Meeeeee ee Meeeeeee; Meeeeee Meeeeeeeee:[88]
Meeeee M: M eeee ee e eeeeee (88 eeee) ee e eeeeeee (88 eM) eee eeeee eee ee eeee ee e eeeeeee eeee ee [Me(MMM8)8](MeM8)8, eeeeeeee ee eeeeee Me8M (88 eM) ee e eeee ee Me(MeM8)8•8M8M (88 e, 88 eeee) ee eee eeeeeee (888 eM) eeee eeeeeeee eee eeeeeee eeee eee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeee eeee eee eeeee (888 eM) eee eee MMe (88 eM). Meeee eeeeeeee eee 88 eee, eeeee (888 eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M/MM8Me8 (8:8, 8 × 888 eM). Mee eeeeeee eee eeeeee eeee M8M (8 × 888 eM), eeeeeeee ee eee. ee MeMMM8 (888 eM); ee eee eeee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee (eeeeee eee, MMMe8/eeeeee 8:8) eeee eee eeeeeee.
Meeeee M: M eeee ee [Me(MMM8)8](MeM8)8 ee MeMM/M8MM/MM8Me8 eee eeeeeeee ee eeeeeeee ee Me8M (8.8 eM, 88 eeee) eee M8MM (88 eeee) ee eeeeeeeeeee Me(MeM8)8•8M8M (8.8 e, 8.8 eeee), eeeeeeee ee MM8Me8 (88 eM). Mee eeeeee (8 eeee) eee eeeee eee ee eeee eee eee eeeeeee eee eeeeeee ee ee eee 8 e. Mee eeeee (88 eM) eee eeeee, eeeeeeee ee eee MMe (88 eM) eee eeeee (888 eM). Meeeeeeeee eeee Me8M (8 × 88 eM), eeeeeee eeee M8M (8 × 888 eM) eee eeee eeee eee. ee MeMMM8 (888 eM), eee eeeeee (Me8MM8), eee eeeeeeee ee eeeeeeeeeeee ee eeeee.
Meeeee M: 8,8-Meeeeeeeeeeeeeee (8.888 e, 8 eeee) eee eeeee ee e eeee ee [Me(MMMe)8]. (MeM8)8 ee MeMM, eeeeeeee ee eeeeeeeeee eeeee Me(MeM8)8 (8.8 e, 88 eeee) ee MeMM (88 eM). Mee eeeeeee eee eeeeee ee 88°M eee 8 e, eeeeee ee ee, eee eeeeee ee ee eeeeeeeee eeeee.
Meeeee M: M eeeeee (8 eeee) eee eeeee ee eee eeeeeee ee e eeee ee [Me(MMM8)8](MeMe8)8 (ee. 8 eeee) ee M8MM/MeMM8, eeeeeeee ee eeeeeeeeee eeeee MeMe8 (8.8 e, 88 eeee) ee M8MM (8 eM) eee MeMM8 (88 eM). Mee eeeeeee eee eeeeee ee 88–88°M eee eee eeeeeeeee eeee (Meeeee 88), eeeeee ee ee, eee eeeeee ee ee eeeeeeeee eeeee.
References
[53] | Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.