European Journal of Organic Chemistry
European Journal of Organic Chemistry
5 years ago

A Remarkable Influence of the Trifluoromethyl Group on the Reactions of -Mercaptoalcohols with Fluorinated -Bromoenones

Heinz Heimgartner, Emilia Obijalska, Grzegorz Mloston, Antonella Capperuzcci, Maria Pawelec, Damiano Tanini
Abstract: Isomeric fluorinated -bromoenones react with dinucleophilic -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. Whereas in the case of 3-bromo-1,1,1-trifluorobut-3-en-2-ones derivatives of 1,4-oxathianes were formed, the 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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701752

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