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Paper | Regular issue | Vol 71, No. 11, 2007, pp.2389-2395
Published online, 27th July, 2007
DOI: 10.3987/COM-07-11125
The Oxidation of Benzo[b]thiophene Derivatives with DDQ — Preparation of π-Extended Hemithioindigoid Compounds

Hiroyuki Endo, Kinji Nagahama, Hidetsugu Wakabayashi, Makoto Kanazumi, Tatsuhisa Kato, and Keiji Kobayashi*

*Department of Chemistry, Graduate School of Material Science, Josai University, Sakado, Saitama 350-0295, Japan

Abstract

Hemithioindigoid compounds, e. g., 2-(6H-cyclopenta[1,2-b:4,3-b’]- bis[1]benzothiophen-6-ylidene)benzo[b]thiophene-3(2H)-one (1), were synthesized in good yields by the oxidation of benzo[b]thiophene derivatives such as 9-(2-benzo[b]thienyl)fluorene with DDQ in the presence of acid and under atmospheric oxygen. Under nitrogen, on the other hand, the reaction of 3 with DDQ resulted in an oxidative dimerization, the product of which was revealed to be equilibrated with radical species.