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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 6
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Original Articles

Oxidative Coupling of Carbon Acid Compounds by Means of Ag2O

Yoshihiko Ito Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan
,
Syotaro Fujii Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan
,
Toshiro Konoike Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan
&
Takeo Saegusa Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto, 606, Japan
Pages 429-433 | Received 17 May 1976, Published online: 06 Dec 2006
 
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Abstract

Transition-metal catalyzed coupling of carbanions by means of transition metal compounds has constituted a convenient method of the carbon-carbon bond formation in organic synthesis.1 Recently, CuCl2-promoted coupling of lithium enolates of ketones2 and esters3 has been reported, which provides new routes to 1,4-diketones and succinate derivatives, respectively. Now we found that some carbon acids, such as acylacetate and monosubstituted malonate, were readily oxidatively dimerized by Ag2O without intervention of their carbanions in dimethyl sulfoxide (DMSO) according to eq. 1.

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