Synlett 2005(16): 2507-2509  
DOI: 10.1055/s-2005-872685
LETTER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 15 July 2005
Publication Date:
21 September 2005 (online)

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.