Anodic Cyanation of β-Dicarbonyl Compounds

Mitsuhiro Okimoto; Kaori Numata; Yukio Takahashi; Masayuki Hoshi; Kenta Tomozawa; Takamasa Shigemoto

doi:10.1055/s-2005-872685

LETTER

Anodic Cyanation of β-Dicarbonyl Compounds

Mitsuhiro Okimoto*, Kaori Numata, Yukio Takahashi, Masayuki Hoshi, Kenta Tomozawa, Takamasa Shigemoto
Department of Applied and Environmental Chemistry, Kitami Institute of Technology, Koen-cyo 165, Kitami, Hokkaido 090-8507, Japan
Fax: +81(157)247719; e-Mail: oki@chem.kitami-it.ac.jp;

Abstract

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Abstract

Several β-dicarbonyl compounds were electrochemically oxidized in a methanolic solution in the presence of sodium cyanide and sodium methoxide to yield the corresponding α-cyano-β-dicarbonyl compounds in moderate to good yields. Presumably, a two-electron transfer transforms the anion derived from the β-dicarbonyl compounds into a cation, which then reacts with a cyanide ion to afford the cyanation products.

Key words

oxidation - ketones - esters - nitriles - cations

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