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Paper | Special issue | Vol 86, No. 1, 2012, pp.305-315
Published online, 25th May, 2012
DOI: 10.3987/COM-12-S(N)10
Synthesis and Redox Behavior of Cyanovinyl-Substituted 2H-Cyclohepta[b]furan-2-ones

Taku Shoji,* Junya Higashi, Shunji Ito, Mitsunori Oda, Masafumi Yasunami, and Noboru Morita

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto 390-8621, Japan

Abstract

Cyanovinyl-substituted 2H-cyclohepta[b]furan-2-ones 3, 4, 5 and 7 were prepared by the Wittig, Knoevenagel and electrophilic substitution reaction, respectively. The intramolecular charge-transfer (ICT) interactions between the 2H-cyclohepta[b]furan-2-one ring and cyanovinyl acceptor moiety were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of these novel compounds was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Significant color changes in these compounds were observed under electrochemical reduction conditions by visible spectroscopy.