Abstract
It was established by IR spectroscopy and quantum-chemical calculations along nonempirical DFT method in B3LYP version with the basis set 6-311 G(d,p) that 2,2-dibromovinyl trifluoromethyl ketone consisted of a mixture of s-cis planar conformer and s-trans-form deviating from a plane by 13°, whereas the s-cis-form is more energetically stable than the s-trans one (ΔE -5.07 kcal mol- 1). Also in 2,2-dibromovinyl methyl ketone the planar s-cis conformer is more stable. Chlorine-containing analogs, 2,2-dichlorovinyl trifluoromethyl ketone and 2,2-dichlorovinyl methyl ketone, are more stable in the planar s-trans-conformation. Charge distribution and polarization in the dibromovinyl ketones are analogous to those in dichlorovinyl ketones in agreement with the established reactivity of dibromovinyl trifluoromethyl ketone. By reaction of 2,2-dibromovinyl trifluoromethyl ketone with 2,4-dinitrophenyl-, alkylhydrazines, N,N-dimethylhydrazine, N,N-, N,O-, N,S-binucleophiles were respectively obtained hydrazone, derivatives of pyrazole, imidazole, oxazole, and 1,3-thiazine containing a trifluoromethyl group.
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Bozhenkov, G.V., Frolov, Y.L., Toryashinova, D.S.D. et al. Structure and Properties of 2,2-Dibromovinyl Trifluoromethyl Ketone. Russian Journal of Organic Chemistry 39, 807–813 (2003). https://doi.org/10.1023/B:RUJO.0000003156.65761.7b
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DOI: https://doi.org/10.1023/B:RUJO.0000003156.65761.7b