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Please login to access the full content or check if you have access via23.14.1.1.7.2 Variation 2: Ultrasound-Assisted Wolff Rearrangement
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Tidwell, T. T., Science of Synthesis, (2006) 23, 586.
Ultrasound assists the silver benzoate induced Wolff rearrangement of diazo ketones 101 to form monoalkylketenes 102 that are captured by the solvent to form the corresponding esters 103 (Scheme 32).[87] Ultrasound can also be used for Wolff rearrangements in which the diazo ketones are prepared by using diazo(trimethylsilyl)methane[88] and for synthesis of 9-fluorenylmethoxycarbonyl-protected β-amino acid derivatives in yields of 65–82%.[89]
Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeee Meeeeeeee ee Meeeee-Meeeeeeee Meeee Meeeeeeeeeeee ee Meeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeeee Meeeeeeeee 888 eeee Meeee Meeeeee; Meeeeee Meeeeeeee:[88]
Me eeeeeee (8 eM) ee e eeeeeeee eeee ee MeMMe (8 e) ee Me8M (8.8 e) eee eeeee ee e eeee ee e eeeee eeeeee 888 (888 ee) ee MeMM (88 eM). Mee eeeeeee eee eeeeeeeee ee eeeeeeeeee (888-M Meeee-eeee, eeeeeee eeeee eeeeeee 888 M, eeeeeeee eeee eeeeeeee 88 ee, eeee eeeeeeeee) eeeee eeeeeeee eeee eee eeeeeeeeeee eee eee eeee ee eeee eeee 8°M. Mee eeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Meee eeeeeeeeee, eee eeee eee eeeeeeee, eeeeeeeeeeee, eee eeeeeeeee ee eeeeeeeeeeeeee; eeeee: 88–88%.[88]
References
| [87] | Meeee, M.-M.; Meeee, M.; Meeeee, M.; Meeee, M.-M.; Meeeeee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [88] | Meeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [89] | Müeeee, M.; Meee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
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