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Communication | Special issue | Vol 25, No. 1, 1987, pp.83-88
Published online, 1st January, 1970
DOI: 10.3987/S-1987-01-0083
Synthesis and Electrochemical Behavior of 1,4-Dithiin Ring Condensed Systems

Toyonari Sugimoto, Iwao Sugimoto, Akihiko Kawashima, Yukishi Yamamoto, Yohji Misaki, and Zen-ichi Yoshida

*Faculty of Engineering, Kyoto University, Yoshida, Sakyou-ku, Kyoto 606-8501, Japan

Abstract

Alkylthio-substituted derivatives of 1,4-dithiin (1a), 1,4,5,8-tetrathianaphthalene (2a), 1,4,5,6,9,10-hexathiaanthracene (3a) and 1,4,5,6,7,10,11,12-octathianaphthacene (4a) are synthesized by Diels-Alder reaction of cis-1,2-dialkylthioethylenes or 2a with dimethyl tetrathiooxalate (6a) and the successive dehydrogenation with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). The electrochemical behavior of the new compounds (1b, 2b, 3b and 4b) and 2a is investigated by cyclic voltammetry. The skeletal rearrangement of 2a to tetrathiafulvalene (TTF) via the dication state, is found to occur by electrochemical or chemical means.