Synthesis p. 377 - 379 (1987)
Update date:2022-07-30
Topics:
Torii, Sigeru
Inokuchi, Tsutomu
Hirata, Youzou
Indirect electrooxidation of alkynes 1 using ruthenium tetroxide as a mediator, leading to 1,2-diones 2 in 72-87percent, 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 deg C.The synthetic utility of this electrochemical oxidation is exemplified by the preparation of 2i (82percent), a key intermediate for the synthesis of furaneol 4, from the commercially available 1i.
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Doi:10.1016/S0022-1139(00)81999-5
(1987)Doi:10.1002/hlca.19890720721
(1989)Doi:10.1055/s-1987-27846
(1987)Doi:10.1021/ja01508a026
(1960)Doi:10.1246/bcsj.81.1605
(2008)Doi:10.1021/ja00020a066
(1991)