Abstract
Oxidation of β-(trifluoroacetyl)vinyl sulfides afforded a series of the corresponding sulfones. The reactions of sulfones with various alkyl- and arylthiols were studied. These reactions provide the basis for a new procedure for the synthesis of β-(trifluoroacetyl)vinyl sulfides.
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R. V. C. Carr and L. A. Paquette, J. Am. Chem. Soc., 1980, 102, 853.
N. S. Simpkins, Tetrahedron, 1990, 46, 6951; O. De Lucchi and L. Pasquato, Tetrahedron, 1988, 44, 6755.
B. M. Trost, H. C. Arndt, P. E. Strege, and T. R. Verhoeven, Tetrahedron Lett., 1976, 3477.
L. A. Paquette, R. V. C. Carr, M. C. Boehm, and R. Gleiter, J. Am. Chem. Soc., 1980, 102, 1186.
L. A. Paquette and R. V. C. Carr, J. Am. Chem. Soc., 1980, 102, 7553.
O. De Lucchi and L. Pasquato, Gazz. Chim. Ital., 1984, 114, 349.
L. A. Paquette and R. V. Williams, Tetrahedron Lett., 1981, 22, 4643.
R. V. C. Carr, R. V. Williams, and L. A. Paquette, J. Org. Chem., 1983, 48, 4976.
O. De Lucchi, V. Lucchini, L. Pasquato, and G. Modena, J. Org. Chem., 1984, 49, 596.
U. Azzena, S. Cossu, O. De Lucchi, and G. Melloni, Tetrahedron Lett., 1989, 30, 1845.
N. Ono, A. Kamimura, and A. Kaji, Tetrahedron Lett., 1986, 27, 1595.
N. Ono, A. Kamimura, and A. Kaji, J. Org. Chem., 1988, 53, 251.
H. Kenji, Y. Mitsuaki, O. Satoru, and K. Ken, J. Am. Chem. Soc., 1984, 106, 6735.
T. A. Bryson, R. E. Dardis, and R. B. Gammill, Tetrahedron Lett., 1978, 8, 743.
H. N. Unn and S. Lars, J. Chem. Soc., Perkin Trans. 1, 1999, 21, 3085.
V. G. Nenajdenko and E. S. Balenkova, Tetrahedron., 1994, 50, 12407.
M. Hojo, R. Masuda, and Y. Kamitori, Tetrahedron Lett., 1976, 13, 1009.
N. P. Petukhova, N. E. Dontsova, O. M. Sazonova, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 2654 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978, 27, 2376 (Engl. Transl.)].
N. P. Petukhova, N. E. Dontsova, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 2327 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982, 31 (Engl. Transl.)].
C. G. Venier, T. G. Squires, and Y. J. Chen, J. Org. Chem., 1982, 47, 3773.
V. G. Nenaidenko, A. V. Sanin, A. V. Churakov, J. A. K. Howard, and E. S. Balenkova, Khim. Geterotsikl. Soedin., 1999, 618 [Chem. Heterocycl. Compd., 1999 (Engl. Transl.)].
A. L. Krasovsky, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2001, 57, 201.
V. G. Nenajdenko, A. L. Krasovsky, M. L. Lebedev, and E. S. Balenkova, Synlett, 1997, 12, 1349.
A. L. Krasovskii, V. G. Nenaidenko, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2001, 1329 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1395].
K. M. Gough and J. Millington, Can. J. Chem., 1995, 73, 1287.
T. Moriguchi, T. Endo, and T. Takata, J. Org. Chem., 1995, 60, 3523.
M. Hojo, R. Masuda, Y. Kamitori, and E. Okada, J. Org. Chem., 1991, 56, 1975.
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Krasovsky, A.L., Nenajdenko, V.G. & Balenkova, E.S. Synthesis of β-trifluoroacetyl-substituted vinyl sulfones and vinyl sulfides. Russian Chemical Bulletin 51, 2080–2085 (2002). https://doi.org/10.1023/A:1021620228529
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DOI: https://doi.org/10.1023/A:1021620228529