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Synthesis 1986; 1986(7): 544-547
DOI: 10.1055/s-1986-31696
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2-Substituted 1,3-Benzoxathiolium Tetrafluoroborates as Efficient Acylating Agents for N,N-Dialkylarylamines

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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Publication Date:
20 August 2002 (online)

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2-Substituted 1,3-benzoxathiolium tetrafluoroborates were used as efficient masked acylating agents for N,N-dialkylarylamines in a two-step reaction. In most of the cases intermediate 2,2-disubstituted 1,3-benzoxathioles were obtained in high yields (about 90%) and their hydrolysis afforded the corresponding ketones in almost quantitative yields. The new procedure offers the following advantages: (1) the reaction conditions are mild; (2) the acylation proceeds selectively at the para-position as referred to the dialkylamino group; (3) the introduction of a tertiary group is easily accomplished.