European Journal of Organic Chemistry p. 3716 - 3723 (2018)
Update date:2022-07-30
Topics:
Obijalska, Emilia
Pawelec, Maria
Mlostoń, Grzegorz
Capperucci, Antonella
Tanini, Damiano
Heimgartner, Heinz
Isomeric fluorinated α-bromoenones react with dinucleophilic β-mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S-heterocycles or non-cyclic products were obtained. With 3-bromo-1,1,1-trifluorobut-3-en-2-ones derivatives of 1,4-oxathianes were formed, but isomeric 2-bromo-4,4,4-trifluorobut-2-en-1-ones yielded 1,3-oxathiolanes or non-cyclic sulfides. The thia-Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.
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