Isomeric fluorinated α-bromoenones react with dinucleophilic beta-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 noncyclic 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.
A Remarkable Influence of a Trifluoromethyl Group on the Reactions of beta-Mercaptoalcohols with Fluorinated α-Bromoenones / Emilia Obijalska; Maria Pawelec; Grzegorz Mlostoń; Antonella Capperucci; Damiano Tanini; Heinz Heimgartner. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - ELETTRONICO. - ..:(2018), pp. 3716-3723. [10.1002/ejoc.201701752]
A Remarkable Influence of a Trifluoromethyl Group on the Reactions of beta-Mercaptoalcohols with Fluorinated α-Bromoenones
Antonella Capperucci;Damiano Tanini;
2018
Abstract
Isomeric fluorinated α-bromoenones react with dinucleophilic beta-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 noncyclic 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.File | Dimensione | Formato | |
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