Abstract
Addition reactions of perfluorothiolacetic acid (TFTAA) with selected organic compounds were studied and six compounds containing the trifluoroacetyl group have been prepared. Two types of reactions were observed, free radical and nucleophilic addition. Under the influence of ultraviolet light, TFTAA (CF 3COSH) adds to olefins to form 1:1 adducts. The CF 3 COS· radical appears to be the adding species. Three new olefin adducts were prepared: CF 3COSCFHCF 2H, CF 3COSCH 2CF 2H, and CF 3COSCH 2CFH 2. In addition, this was found to be a new way to prepare CF 3COSCH 2CH 3, which had been previously prepared by another route. Physical constants, analytical data, infrared, ultraviolet, NMR and mass spectra are presented supporting the proposed structures for these compounds. Nucleophilic addition adducts were formed with TFTAA. TFTAA is a strong acid and the CF 3COS − ion was found to act as a nucleophile with several substrates. With hexafluoroacetone, addition of TFTAA across the carbonyl group gave CF 3COSC(CF 3) 2OH, and with ethylene oxide the alcohol addition product, CF 3COSCH 2CH 2OH, was produced.
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