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Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine
Authors:Shoji Matsumoto  Daiki TakadaHirokazu Kageyama  Motohiro Akazome
Affiliation:Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoicho, Inageku, Chiba 263-8522, Japan
Abstract:Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the corresponding product was also obtained in a polar solvent. Single crystal X-ray analysis revealed that the benzo[c]thiophen-1-aminium structure possesses a resonance structure in N–C–S bond. Its stabilization shows a clear difference in the result from the reaction of amide analogue with iodine to give no stable compound.
Keywords:Thioamide   Iodine   Triple bond   Cyclization reaction
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