Electrochemical generation of [PhSeF] for fluoro-selenation of alkenes and alkynes and its recycle use

Electrochimica Acta

Volumn 42, Issue 13-14, 1997, Pages 2005-2007

  Uneyama, Kenji ^a   Asai, Hideki ^a   Dan Oh, Yasufumi ^a   Matta, Hirokazu ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Electrochemical recycle; Fluoro selenation

Indexed keywords

ELECTROCHEMISTRY; ELECTROLYSIS; OLEFINS; OXIDATION; REACTION KINETICS; SELENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ELECTROCHEMICAL RECYCLE; FLUOROSELENATION; FLUOROSELENIDES;

FLUORINE COMPOUNDS;

EID: 0030697619     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0013-4686(97)85474-6     Document Type: Article

References (28)

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16. 3N·3HF is currently used in various electrochemical reactions; E. Laurent, B. Marquet, R. Tardivel and H. Thiebault, Tetrahedron Lett. 28, 2359 (1987); L. Kabore, S. Chebli, R. Faure, E. Laurent and B. Marquet, ibid. 31, 3137 (1990); E. Laurent, B. Marquet and R. Tardivel, Tetrahedron 47, 3969 (1991); T. Brigaud and E. Laurent, Tetrahedron Lett. 31, 2287 (1990); T. Fuchigami, T. Hayashi and A. Konno, ibid. 33, 3161 (1992); M. Hanack and B. Wilhelm, Angew. Chem. Int. Ed. Engl. 28, 1057 (1989); T. Fuchigami, S. Narizuka and A. Konno, J. Org. Chem. 57, 3755 (1992).
17. 3N·3HF is currently used in various electrochemical reactions; E. Laurent, B. Marquet, R. Tardivel and H. Thiebault, Tetrahedron Lett. 28, 2359 (1987); L. Kabore, S. Chebli, R. Faure, E. Laurent and B. Marquet, ibid. 31, 3137 (1990); E. Laurent, B. Marquet and R. Tardivel, Tetrahedron 47, 3969 (1991); T. Brigaud and E. Laurent, Tetrahedron Lett. 31, 2287 (1990); T. Fuchigami, T. Hayashi and A. Konno, ibid. 33, 3161 (1992); M. Hanack and B. Wilhelm, Angew. Chem. Int. Ed. Engl. 28, 1057 (1989); T. Fuchigami, S. Narizuka and A. Konno, J. Org. Chem. 57, 3755 (1992).
18. 3N·3HF is currently used in various electrochemical reactions; E. Laurent, B. Marquet, R. Tardivel and H. Thiebault, Tetrahedron Lett. 28, 2359 (1987); L. Kabore, S. Chebli, R. Faure, E. Laurent and B. Marquet, ibid. 31, 3137 (1990); E. Laurent, B. Marquet and R. Tardivel, Tetrahedron 47, 3969 (1991); T. Brigaud and E. Laurent, Tetrahedron Lett. 31, 2287 (1990); T. Fuchigami, T. Hayashi and A. Konno, ibid. 33, 3161 (1992); M. Hanack and B. Wilhelm, Angew. Chem. Int. Ed. Engl. 28, 1057 (1989); T. Fuchigami, S. Narizuka and A. Konno, J. Org. Chem. 57, 3755 (1992).
19. 3N·3HF is currently used in various electrochemical reactions; E. Laurent, B. Marquet, R. Tardivel and H. Thiebault, Tetrahedron Lett. 28, 2359 (1987); L. Kabore, S. Chebli, R. Faure, E. Laurent and B. Marquet, ibid. 31, 3137 (1990); E. Laurent, B. Marquet and R. Tardivel, Tetrahedron 47, 3969 (1991); T. Brigaud and E. Laurent, Tetrahedron Lett. 31, 2287 (1990); T. Fuchigami, T. Hayashi and A. Konno, ibid. 33, 3161 (1992); M. Hanack and B. Wilhelm, Angew. Chem. Int. Ed. Engl. 28, 1057 (1989); T. Fuchigami, S. Narizuka and A. Konno, J. Org. Chem. 57, 3755 (1992).
20. 3N·3HF is currently used in various electrochemical reactions; E. Laurent, B. Marquet, R. Tardivel and H. Thiebault, Tetrahedron Lett. 28, 2359 (1987); L. Kabore, S. Chebli, R. Faure, E. Laurent and B. Marquet, ibid. 31, 3137 (1990); E. Laurent, B. Marquet and R. Tardivel, Tetrahedron 47, 3969 (1991); T. Brigaud and E. Laurent, Tetrahedron Lett. 31, 2287 (1990); T. Fuchigami, T. Hayashi and A. Konno, ibid. 33, 3161 (1992); M. Hanack and B. Wilhelm, Angew. Chem. Int. Ed. Engl. 28, 1057 (1989); T. Fuchigami, S. Narizuka and A. Konno, J. Org. Chem. 57, 3755 (1992).
21. 3N·3HF is currently used in various electrochemical reactions; E. Laurent, B. Marquet, R. Tardivel and H. Thiebault, Tetrahedron Lett. 28, 2359 (1987); L. Kabore, S. Chebli, R. Faure, E. Laurent and B. Marquet, ibid. 31, 3137 (1990); E. Laurent, B. Marquet and R. Tardivel, Tetrahedron 47, 3969 (1991); T. Brigaud and E. Laurent, Tetrahedron Lett. 31, 2287 (1990); T. Fuchigami, T. Hayashi and A. Konno, ibid. 33, 3161 (1992); M. Hanack and B. Wilhelm, Angew. Chem. Int. Ed. Engl. 28, 1057 (1989); T. Fuchigami, S. Narizuka and A. Konno, J. Org. Chem. 57, 3755 (1992).
22. Ethyl 4-hydroxy-5-phenylselenopentanoate and 4-phenylselenomethyl-γ-butyrolactone were isolated as major products.
23. 19F NMR chart with known experimental data cited in references 2(b) and 4.
24. S. Torii, K. Uneyama, M. Ono and T. Bannou, J. Am. Chem. Soc. 103, 4606 (1981); K. Uneyama, M. Ono and S. Torii, Phosphorus and Sulfur 16, 35 (1983).
25. S. Torii, K. Uneyama, M. Ono and T. Bannou, J. Am. Chem. Soc. 103, 4606 (1981); K. Uneyama, M. Ono and S. Torii, Phosphorus and Sulfur 16, 35 (1983).
26. Difluoroselenanes are readily hydrolyzed by air moisture to the corresponding selenoxides. A. M. Foster, Y. L. Douns, Polyhedron 4, 1625 (1985); Y. L. Yagupolskii and T. L. Savina, Zh. Org. Khim. 15, 438 (1979); (Chem. Abstr. 90, 203618).
27. Difluoroselenanes are readily hydrolyzed by air moisture to the corresponding selenoxides. A. M. Foster, Y. L. Douns, Polyhedron 4, 1625 (1985); Y. L. Yagupolskii and T. L. Savina, Zh. Org. Khim. 15, 438 (1979); (Chem. Abstr. 90, 203618).
28. Difluoroselenanes are readily hydrolyzed by air moisture to the corresponding selenoxides. A. M. Foster, Y. L. Douns, Polyhedron 4, 1625 (1985); Y. L. Yagupolskii and T. L. Savina, Zh. Org. Khim. 15, 438 (1979); (Chem. Abstr. 90, 203618).