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23.14.1.1.7.2 Variation 2: Ultrasound-Assisted Wolff Rearrangement

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623586.

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 6582%.[‌89‌]

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