S. Matsumoto, Daiki Takada, Hirokazu Kageyama
Jan 29, 2014
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron Letters
Abstract
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.