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Synthesis 1987; 1987(4): 377-379
DOI: 10.1055/s-1987-27950
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A Simple and Improved Procedure for the Conversion of Alkynes to 1,2-Diketones by Indirect Electrooxidation With Ruthenium Tetroxide as a Mediator

Sigeru Torii* , Tsutomu Inokuchi, Youzou Hirata
  • *Department of Industrial Chemistry, School of Engineering, Okayama University, Okayama 700, Japan
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Publication Date:
20 August 2002 (online)

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Indirect electrooxidation of alkynes 1 using ruthenium tetroxide as a mediator, leading to 1,2-diones 2 in 72-87%, is described. The electrolysis is carried out in the presence of a catalytic amount of ruthenium dioxide dihydrate in a two phase system of saturated aqueous sodium chloride and carbon tetrachloride. The overoxidation of 1,2-diones to the corresponding carboxylic acid, an unavoidable drawback generally encountered in the metal oxidation of acetylenes, is suppressed greatly by maintaining the pH of the aqueous phase at 4 and conducting the reaction at 0-5°C. The synthetic utility of this electrochemical oxidation is exemplified by the preparation of 2i (82%), a key intermediate for the synthesis of furaneol 4, from the commercially available 1i.

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