Ruff dismantling

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The Ruff breakdown , also Ruff-Fenton breakdown , is an oxidative decarboxylation of aldoses , named after Otto Ruff .

In the first step the sugar 1 (a schematically drawn aldose) is oxidized to an aldonic acid 2 by aqueous bromine solution . In the second step, the carboxy group is split off with hydrogen peroxide and iron (III). The now terminal carbon atom , which previously had a hydroxyl group , is oxidized to an aldehyde function in this step 3 . The carbon chain of aldose 1 is shortened by one carbon atom, creating aldose 3 .

General scheme of Ruff dismantling. Please see text for details.

For example, this method can be used to decarboxylate D - glucose (a hexose ) to D - arabinose (a pentose ).

literature

  • K. Peter C. Vollhardt, Neil E. Schore: Organic Chemistry, 4th Edition, Wiley-VCH GmbH & Co. KGaA, Weinheim, ISBN 3-527-31380-X .