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Tetrapropylammonium perruthenate catalyzed glycol cleavage to carboxylic (di)acids
Andrea-Katharina C Schmidt1, Christian B W Stark
1Fakultät für Chemie und Mineralogie, Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany.
Abstract:
A new method to accomplish glycol cleavage to carboxylic (di)acids in one step using catalytic amounts of tetrapropylammonium perruthenate (TPAP) together with N-methylmorpholine N-Oxide (NMO) as the stoichiometric oxidant is presented. In addition to regenerating the active catalyst, the N-oxide stabilizes intermediary carbonyl hydrates and thereby shifts a crucial equilibrium. The mild oxidation protocol is applicable to a broad range of substrates providing the respective acids, diacids, or keto acids in high yields.
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