Thiophilic nucleophilic trifluoromethylation of α-substituted dithioesters. Access to S-trifluoromethyl ketene dithioacetals and their reactivity with electrophilic species

Journal of Fluorine Chemistry

Volumn 134, Issue , 2012, Pages 164-171

  Gouault Bironneau, Sonia ^a   Timoshenko, Vadim M ^a,b   Grellepois, Fabienne ^a   Portella, Charles ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

Dithioesters; Fluorine; Ketene dithioacetals; Sulfur; Thiophilic addition; Trifluoromethylation

Indexed keywords

EID: 84856091787     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2011.02.016     Document Type: Article

References (22)

1. P. Metzner Top. Curr. Chem. 204 Organosulfur Chemistry I 1999 127 181
2. P. Beak, and J.W. Worley J. Am. Chem. Soc. 94 1972 597 604
3. C. Portella, M. Muzard, J.-P. Bouillon, C. Brule, F. Grellepois, Y.G. Shermolovich, V.M. Timoshenko, A.N. Chernega, E. Sotoca-Usina, M. Parra, and S. Gil Heteroatom Chem. 18 2007 500 508
4. S.S. Mikhailichenko, A.V. Rudnichenko, V.M. Timoshenko, A.N. Chernega, Y.G. Shermolovich, F. Grellepois, and C. Portella J. Fluorine Chem. 128 2007 703 709
5. F. Grellepois, V.M. Timoshenko, Y.G. Shermolovich, and C. Portella Org. Lett. 8 2006 4323 4326
6. V.M. Timoshenko, Y.G. Shermolovich, F. Grellepois, and C. Portella J. Fluorine Chem. 127 2006 471 475
7. C. Portella, and Y.G. Shermolovich Tetrahedron Lett. 38 1997 4063 4064
8. V.M. Timoshenko, and C. Portella J. Fluorine Chem. 130 2009 586 590
9. CCDC 805008 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
10. S.D. Lee, T.H. Chan, and K.S. Kwon Tetrahedron Lett. 25 1984 3399 3402
11. J.D. White, T.R. Vedananda, M. Kang, and S.C. Choudhry J. Am. Chem. Soc. 108 1986 8105 8107
12. R.A. Holton, C. Somoza, H.-B. Kim, F. Liang, R.J. Biediger, P. Douglas Boatman, M. Shindo, C.C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K.K. Murthi, L.N. Gentile, and J.H. Liu J. Am. Chem. Soc. 116 1994 1597 1598
13. D. Hoppe, and A. Broenneke Synthesis 1982 1045 1048
14. C. Derwing, H. Frank, and D. Hoppe Eur. J. Org. Chem. 1999 3519 3524
15. I. Kieltsch, P. Eisenberger, and A. Togni Angew. Chem. Int. Ed. 46 2007 754 757
16. K.O. Christe, W.W. Wilson, R.D. Wilson, R. Bau, and J. Feng J. Am. Chem. Soc. 112 1990 7619 7625
17. Y. Kita, J.-I. Haryta, T. Fujii, J. Segawa, and Y. Tamura Synthesis 1981 451 452
18. E.J. Corey, and A. Venkateswarlu J. Am. Chem. Soc. 94 1972 6190 6191
19. M.N. Nassar, B.J. Agha, and G.A. Digenis J. Labelled Compd. Radiopharm. 23 1986 667 676
20. L. Panella, B.L. Feringa, J.G. de Vries, and A.J. Minnaard Org. Lett. 7 2005 4177 4180
21. G.A. Russell, and L.A. Ochrymowycz J. Org. Chem. 35 1970 764 770
22. A.R. Katritzky, D. Toader, and L. Xie Synthesis 1996 1425 1427