Functionalization of alkenes by polyfluorinated α,β-unsaturated sulphenyl chlorides: Dual reactivity of perfluoro-2-methyl-2-penten-3-yl sulphenyl chloride in reactions with activated olefins

Journal of Fluorine Chemistry

Volumn 77, Issue 2, 1996, Pages 183-191

  Popkova, V Ya ^a   Osmanov, V K ^b   Borisov, A V ^b   Ugrak, B I ^a   Bodrikov, I V ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b NIZHNY NOVGOROD STATE TECHNICAL UNIVERSITY N A R E ALEKSEEV   (Russian Federation)

Author keywords

Activated olefins; Alkene functionalization; Dual reactivity; IR spectroscopy; Mass spectrometry; NMR spectroscopy; Polyfluorinated , unsaturated sulphenyl chloride

Indexed keywords

EID: 16144367910     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-1139(96)03425-2     Document Type: Article

References (29)

1. [1] For previous communication, see: (a) V.Ya. Popkova, V K. Osmanov, A.V. Borisov, A.I. Lutsenko, A.F. Aerov, E.I. Mysov, M.V. Galachov and I.V. Bodrikov, J. Fluorine Chem., 65 (1993) 181;
2. (b) V.K. Osmanov, Ph.D. Thesis, Nizhegorodskii State Technical University, Nizhnii Novgorod, 1993;
3. (c) V.Ya. Popkova, Professor Thesis, INEOS, Russian Academy of Science, Moscow, 1995.
4. [2] (a) R.A. Bekker and V.Ya. Popkova, Izv. Akad. Nauk SSSR, Ser. Khim., (1982) 1123; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1982) 1001;
5. [2] (a) R.A. Bekker and V.Ya. Popkova, Izv. Akad. Nauk SSSR, Ser. Khim., (1982) 1123; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1982) 1001;
6. (b) V.Ya. Popkova, M.V. Galakhov and I.L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., (1989) 116; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1989) 104.
7. (b) V.Ya. Popkova, M.V. Galakhov and I.L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., (1989) 116; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1989) 104.
8. [3] V.Ya. Popkova, V.F. Snegirev, M.Yu. Antipin and Yu.T. Struchkov, Izv. Akad. Nauk SSSR, Ser. Khim., (1989) 1123; Bull. Acad. Sci. USSR. Div. Chem. Sci., (1989) 1019.
9. [3] V.Ya. Popkova, V.F. Snegirev, M.Yu. Antipin and Yu.T. Struchkov, Izv. Akad. Nauk SSSR, Ser. Khim., (1989) 1123; Bull. Acad. Sci. USSR. Div. Chem. Sci., (1989) 1019.
10. [4] R.A. Bekker, V.Ya. Popkova and I.L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., (1980) 2175; [Chem. Abs., 94 (1981) 30 232k] - incorrect information, see correction in the CA File on STN International in 1993.
11. [4] R.A. Bekker, V.Ya. Popkova and I.L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., (1980) 2175; [Chem. Abs., 94 (1981) 30 232k] -incorrect information, see correction in the CA File on STN International in 1993.
12. [5] (a) R.A. Bekker, V.Ya. Popkova, V.F. Snegirev and I.L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., (1981) 2167; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1981) 1782;
13. [5] (a) R.A. Bekker, V.Ya. Popkova, V.F. Snegirev and I.L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., (1981) 2167; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1981) 1782;
14. (b) V.Ya. Popkova, V.M. Anisimov, G.N. Dolenko, M.N. Semenenko and V.M. Fedoseev, J. Chem. Soc., Perkin Trans., 2 (1995) 1375, and literature cited therein.
15. [6] L.P. Rasteikiene, D.I. Greiciute, M.G. Lin'kova and I.L. Knunyants, Usp. Khim., 46 (1977) 1041; Russ. Chem. Rev., 46 (1977) 548, and literature cited therein.
16. [6] L.P. Rasteikiene, D.I. Greiciute, M.G. Lin'kova and I.L. Knunyants, Usp. Khim., 46 (1977) 1041; Russ. Chem. Rev., 46 (1977) 548, and literature cited therein.
17. [7] I.V. Bodrikov, A.V. Borisov, W.A. Smit and A.I. Lutsenko, Tetrahedron Lett., 25 (1984) 4983, and literature cited therein.
18. [8] W.L. Orr and N. Kharasch, J. Am. Chem. Soc., 78 (1956) 1201, and literature cited therein.
19. [9] A.V. Borisov, G.N. Borisova, A.I. Lutsenko, V.A. Smit and I.V. Bodrikov, Izv. Akad. Nauk SSSR, Ser. Khim., (1988) 1194; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1988) 1054.
20. [9] A.V. Borisov, G.N. Borisova, A.I. Lutsenko, V.A. Smit and I.V. Bodrikov, Izv. Akad. Nauk SSSR, Ser. Khim., (1988) 1194; Bull. Acad. Sci. USSR, Div. Chem. Sci., (1988) 1054.
21. [10] W.J. Middleton, J. Org. Chem., 30 (1965) 1395.
22. [11] W.J. Middleton, US Pat. 3 012 995, 1961; [Chem. Abs., 56 (1962) 6141g].
23. [11] W.J. Middleton, US Pat. 3 012 995, 1961; [Chem. Abs., 56 (1962) 6141g].
24. [12] J.W. Emsley, J. Feeney and L.H. Sutcliffe, High Resolution NMR Spectroscopy, Pergamon Press, Oxford/London/Edinburgh/New York/Paris/Frankfurt, 1966, Vol. 2; V.F. Bistrov and Yu.N. Cheynker (eds.), Spektroskopiya yadernogo magnitnogo rezonansa visokogo razrecheniya, Mir, Moscow, 1969, Vol. 2, p. 60 (Russ. edn.).
25. [12] J.W. Emsley, J. Feeney and L.H. Sutcliffe, High Resolution NMR Spectroscopy, Pergamon Press, Oxford/London/Edinburgh/New York/Paris/Frankfurt, 1966, Vol. 2; V.F. Bistrov and Yu.N. Cheynker (eds.), Spektroskopiya yadernogo magnitnogo rezonansa visokogo razrecheniya, Mir, Moscow, 1969, Vol. 2, p. 60 (Russ. edn.).
26. [13] (a) Z. Song and P. Beak, J. Am. Chem. Soc., 112 (1990) 8126, and literature cited therein; (b) E.L. Clennan and J.J. Koola, J. Am. Chem. Soc., 115 (1993) 3802, and literature cited therein.
27. [13] (a) Z. Song and P. Beak, J. Am. Chem. Soc., 112 (1990) 8126, and literature cited therein; (b) E.L. Clennan and J.J. Koola, J. Am. Chem. Soc., 115 (1993) 3802, and literature cited therein.
28. [14] C. Mansch, A. Leo and R.W. Taft, Chem. Rev., 91 (1991) 165.
29. [15] N.R. Slobodkin and N. Kharasch, J. Am. Chem. Soc., 82 (1960) 866.