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Paper | Special issue | Vol 88, No. 1, 2014, pp.319-329
Published online, 11th July, 2013
DOI: 10.3987/COM-13-S(S)24
Synthesis, Properties, and Crystal Structure of DDQ-Adducts of Ethynylated 2H-Cyclohepta[b]furan-2-ones

Taku Shoji,* Mitsuhisa Maruyama, Erika Shimomura, Akifumi Maruyama, Shunji Ito, Masafumi Yasunami, Junya Higashi, Kozo Toyota, and Noboru Morita*

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

Abstract

Ethynylated 2H-cyclohepta[b]furan-2-ones reacted with 2,3-dichrolo-5,6-dicyano-1,4-benzoquinone (DDQ) in a formal [2+2] cycloaddition reaction to afford the corresponding DDQ-adducts in good yields. The electronic properties of the DDQ-adducts were investigated by UV/Vis spectroscopy. One of the DDQ-adducts was revealed the molecular structure by X-ray crystallographic analysis. The redox behavior of the new compounds was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV).