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Synthesis 1987; 1987(3): 311-314
DOI: 10.1055/s-1987-27931
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2-Substituted 1,3-Benzoxathiolium Tetrafluoroborates as Useful Acylating Agents of Electron-Rich Aromatic and Heteroaromatic Compounds

Silvano Cadamuro* , Iacopo Degani, Rita Fochi, Antonella Gatti, Valeria Regondi
  • *Istituto di Chimica Organica dell' Università Via Bidone 36, I-10125 Torino, Italy
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Publikationsdatum:
12. September 2002 (online)

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2-Substituted 1,3-benzoxathiolium tetrafluoroborates were used for the two-step acylation of electron-rich aromatic and heteroaromatic compounds: 1,3-dimethoxybenzene, 1,3,5-trimethoxybenzene, pyrrole and indoles. In most of the cases intermediate 2,2-disubstituted 1,3-benzoxathioles were obtained in good to high yields (55-100%) and subsequent hydrolysis of these with mercury(II) oxide and aqueous tetrafluoroboric acid (35%) in tetrahydrofuran afforded the corresponding ketones in almost quantitative yields.