1007105-56-7Relevant academic research and scientific papers
A Remarkable Influence of a Trifluoromethyl Group on the Reactions of β-Mercaptoalcohols with Fluorinated α-Bromoenones
Obijalska, Emilia,Pawelec, Maria,Mlostoń, Grzegorz,Capperucci, Antonella,Tanini, Damiano,Heimgartner, Heinz
, p. 3716 - 3723 (2018/04/09)
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.
Stereoelectronic structure of α-bromoalkenyl trifluoromethyl ketones
Chipanina,Aksamentova,Rulev, A. Yu.
scheme or table, p. 1431 - 1436 (2010/03/24)
The results of quantum-chemical calculations at the B3LYP/6-311G level of theory showed that (Z)-α-bromo-β-arylalkenyl trifluoromethyl ketones are more stable than the corresponding E isomers by 4-5 kcal/mol. Relatively large positive charge on the olefin
Domino transformations of gem-trifluoroacetyl(bromo)alkenes under the action of secondary amines
Rulev, Alexander Yu.,Uchakov, Igor A.,Nenajdenko, Valentin G.,Balenkova, Elisabeth S.,Voronkov, Mikhail G.
, p. 6039 - 6045 (2008/09/17)
2-Bromo-3-arylpropenyl trifluoromethyl ketones underwent aza-Michael/hydroxyalkylation domino reactions triggered by secondary amines to give unexpectedly 2-amino-1-trifluoromethyl indenols in good yields. The process was found to involve the intermediate
