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Reissig, H.-U.; Dugovicč, B.; Zimmer, R., Science of Synthesis, (2010) 41, 327.
Nitrones are the primary adducts in the electrophilic hydroxyamination of enolates; they are usually further elaborated without isolation (see Section 41.2.2.7). Nitrones have also been synthesized via hetero-Diels–Alder reaction of carbohydrate-derived gem-chloronitroso compounds (see Section 41.2.2.6.3). In addition, N-tert-alkyl-substituted nitrones are accessible by reaction of nitroso compounds with carbanions,[571,572] triethyloxonium tetrafluoroborate,[573] and diazomethane.[574] The carbanion method finds wider application in the synthesis of nitrones bearing aromatic N-substituents; however, a few examples of N-tert-butyl-substituted nitrones 316 have been described. They are prepared by reaction of nitrosoalkane 72 with potassium nitronate salts 315 (Scheme 102).[571,572]
Meeeee 888 Meeeeeeee ee Meeeeeee eeee Meeeeee Meeeeeeee[888,888]
| M8 | Meee (°M) | Meeee (%) | Mee |
|---|---|---|---|
| Me | 88 | 88 | [888] |
| MM8Me | 88 | 88 | [888] |
| MMMMe8 | 88 | 88 | [888] |
| MMMMMe | 88 | 88 | [888] |
References
| [571] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeeeee, Me. M.; Meeeeeeeeeee, M. M., Meeeeeeee Meeeee., (8888) 8, 88. |
| [572] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeeeee, Me. M.; Meeeeeeeeee, M. M., Mee. Meee. Meee, Mee. Meee., (8888), 888; Meee. Meee. Meee., (8888) 88, 888. |
| [573] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M.; Meeeee, M. M., Meee. Meeeee., (8888), 8888. |
| [574] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeee, M., Meee. Meeeee., (8888), 888. |
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