Abstract
A route to α-hydropolyfluoroalkanethiols and polyfluorothioacyl halides via thermal splitting of benzyl polyfluoroalkyl sulfides under the action of phosphorus pentoxide was proposed. The thiols obtained were used as starting materials for the synthesis of α-hydropolyfluoroalkanesulfenyl chlorides. The properties of the resulting F,S-containing compounds were studied.
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T. Nguyen and C. Wakselman, J. Fluor. Chem., 1987, 35, 523.
R. A. Bekker, V. Ya. Popkova, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 2347 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982, 31 (Engl. Transl.)].
R. A. Bekker and V. Ya. Popkova, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1898 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 1725 (Engl. Transl.)].
A. N. Kovregin, A. Yu. Sizov, and A. F. Ermolov, Izv. Akad. Nauk, Ser. Khim., 2003, 1134 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1198].
W. J. Middleton and W. H. Sharkey, J. Org. Chem., 1965, 30, 1384.
J. F. Harris and W. A. Sheppard, J. Org. Chem., 1961, 26, 354.
J. F. Harris and F. W. Stacey, J. Chem. Soc., 1963, 85, 749.
Yu. V. Zeifman and L. T. Lantseva, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 1102 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, 29 (Engl. Transl.)].
V. G. Andreev, A. Yu. Sizov, and A. F. Kolomiets, Izv. Akad. Nauk, Ser. Khim., 1994, 80 [Russ. Chem. Bull., 1994, 43 (Engl. Transl.)].
D. Purdela and R. Vilceanu, Chimia compusilor organici ai fosforului si ai acizilor lui, Editura Academiei Republicii Socialiste Romania, 1965, 539 pp.
R. A. Bekker, G. G. Melikyan, B. L. Dyatkin, and I. L. Knunyants, Zh. Org. Khim., 1975, 11, 1370 [J. Org. Chem. USSR, 1975, 11 (Engl. Transl.)].
E. Magnier, M. Tordeux, R. Goumont, K. Magder, and C. Wakselman, J. Fluor. Chem., 2003, 124, 55.
H. Fritz and W. Sundermeyer, Tetrahedron Lett., 1985, 26, 5505.
A. Yu. Sizov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1619 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40 (Engl. Transl.)].
R. C. Terrel, T. Ucciardi, and J. F. Vitcha, J. Org. Chem., 1965, 30, 4011.
R. F. Langer and N. A. Morrison, Can. J. Chem., 1987, 65, 2385.
C. Portella, Y. G. Shermolovich, and O. Tschenn, Bull. Soc. Chim. Fr., 1997, 134, 697.
J. T. Barr and E. Lawlor, US Pat. 2 894 991, 1959; Chem. Abstrs, 1961, 55, 2572.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1156–1163, July, 2006.
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Sizov, A.Y., Kovregin, A.N., Serdyuk, R.N. et al. Synthesis and reactivity of fluorine-containing thiols and thioacyl halides. Russ Chem Bull 55, 1200–1208 (2006). https://doi.org/10.1007/s11172-006-0399-4
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DOI: https://doi.org/10.1007/s11172-006-0399-4