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Abstract
Simple, efficient and selective new one-step transformations with DDQ, IBDA and I2/DMSO are presented for the dehydrogenation of thioflavanone (la), as well as the oxidized (1c) and halogenated (1d) derivatives. Ring-contraction reactions of the 1-oxide lb and Id leading to the formation of the benzothiophen derivatives 3α and 5, respectively, are also described.