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Two-way Homologation Of Aliphatic Aldehydes: Both One-carbon Shortening And Lengthening Via The Same Intermediate

J. W. Yoo, Youngran Seo, J. B. Park, Y. G. Kim
Published 2020 · Chemistry

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Abstract Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
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