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29.17.3.1.2.2 Variation 2: Oxidation Using Selenium Dioxide

DOI: 10.1055/sos-SD-129-00159

Coote, S. C.; Smith, L. H. S.; Procter, D. J.Science of Synthesis Knowledge Updates, (20103466.

Activated methyl or methylene groups may be oxidized by selenium dioxide. For example, the acetyl group in thiophene 161 is oxidized in high yield (87%) to the corresponding α-oxoaldehyde hydrate 162 by reaction with 1 equivalent of selenium dioxide (Scheme 56).[‌191‌] Under very similar conditions, acetone is oxidized in moderate yield to the corresponding tricarbonyl unit 163, which exists as the hydrate 164.[‌192‌]

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References


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