Abstract
CH-acids of general formula CF3CH(X)CF3 (X = CF3, CO2R) react with 2,3-unsaturated alcohols in the presence of bases to give trifluoromethylated products of the [3,3]-sigmatropic rearrangement. These reactions provide a convenient method for the synthesis of 2-alkenyl-2-trifluoromethylmalonates.
Similar content being viewed by others
References
V. G. Andreev and A. F. Kolomiets,Usp. Khim., 1993,62, 594 [Russ. Chem. Rev., 1993,62 (Engl. Transl.)].
S. T. Purrington and S. C. Weeks,J. Fluorine Chem., 1992,56, 165.
V. G. Andreev, A. F. Kolomiets, and A. V. Fokin,J. Fluorine Chem., 1992,56, 259.
I. L. Knunyants, S. T. Kocharyan, Yu. A. Cheburkov, M. D. Bargamova, and E. M. Rokhlin,Dokl. Akad. Nauk SSSR, 1965,165, 827 [Dokl. Chem., 1965,165 (Engl. Transl.)].
S. T. Kocharyan, Ph. D. (Chemistry) Thesis, Inst. of Organoelement Compounds, Acad. Sci. USSR, Moscow, 1968, 142 pp. (in Russian).
C. G. Krespan,Tetrahedron, 1967,23, 4243.
V. G. Andreev, A. F. Kolomiets, and G. A. Sokol'skii,Dokl. Akad. Nauk SSSR, 1980,250, 1386 [Dokl. Chem., 1980,250 (Engl. Transl.)].
S. Andreades,J. Am. Chem. Soc., 1964,86, 2003.
I. L. Knunyants and E. M. Rokhlin,Sov. Sci. Rev., Sect. B, Chem. Rev., 1984,5, 97.
V. G. Andreev, A. F. Kolomiets, and G. A. Sokol'skii,Zh. Org. Khim., 1979,15, 2417 [J. Org. Chem. USSR, 1979,15 (Engl. Transl.)].
V. G. Andreev, A. F. Kolomiets, and A. V. Fokin,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2805 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 2447 (Engl. Transl.)].
InSintezy ftororganicheskikh soedinenii [Synthesis of Organofluorine Compounds], Eds. I. L. Knunyants and G. G. Yakobson, Khimiya, Moscow, 1973, 15 (in Russian).
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1273–1277, July, 1994.
Rights and permissions
About this article
Cite this article
Andreev, V.G. A new approach to the synthesis of trifluoromethylated products of the [3,3]-sigmatropic rearrangement. Russ Chem Bull 43, 1209–1213 (1994). https://doi.org/10.1007/BF00698247
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00698247