Reactions of polyfluorinated thietanes. Selective synthesis of 4-R-2,2-bis(trifluoromethyl)thietane-1-S-oxides and 2-substituted 5-fluoro-4-(trifluoromethyl)-2,3-dihydrothiophenes

Journal of Fluorine Chemistry

Volumn 130, Issue 9, 2009, Pages 780-787

  Petrov, Viacheslav A ^a   Marshall, William J ^a  

^a DUPONT COMPANY   (United States)

Author keywords

2 Alkoxy 5 fluoro 4 (trifluoromethyl) 2,3 dihydrothiophenes; 2 Fluoro 3 trifluoromethyl thiophene; 4 Alkoxy 2,2 bis(trifluoromethyl)thietane 1 S oxides; 4 Alkoxy 2,2 bis(trifluoromethyl)thietanes; Oxidation; Reductive defluorination

Indexed keywords

EID: 69249214123     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.06.011     Document Type: Article

References (39)

1. Middleton W.J. J. Org. Chem. (1965) 1395-1398
2. England D.C. J. Org. Chem. 46 (1981) 153-157
3. Kitazume T., Otaka T., Takei R., and Ishikawa N. Bull. Chem. Soc. Jpn. 49 (1976) 2491-2494
4. Postovoi S.A., Vol'pin I.M., Delyagina N.I., Galakhov M.V., Zeifman Y.V., and German L.S. Izv. Akad. Nauk. SSSR, Ser. Khim. (1989) 1380-1383
5. Petrov V.A., Krespan C.G., and Marshall W. J. Fluorine Chem. 126 (2005) 1332-1341
6. M.S. Raasch, E.I. (du Pont de Nemours & Co.), US Patent 3406184, 1968.
7. Raasch M.S. J. Org. Chem. 35 (1970) 3470-3483
8. Petrov V.A. ACS Symp. Ser. 1003 (2009) 105-133
9. Petrov V.A. Mendeleev Commun. (2006) 155-157
10. Smart B.E., and Middleton W.J. J. Am. Chem. Soc. 109 (1987) 4982-4992
11. T. Brenna, M. Hendrick, Pfizer Inc., US Patent 4,411,925, 1983.
12. Petrov V.A., Lustig S., and Marshall W. J. Fluorine Chem. 128 (2007) 1227-1234
13. Elsaesser A., Sundermeyer W., and Stephenson D.S. Chem. Ber. 118 (1985) 116-123
14. Hiyama T. Organofluorine Compounds. Chemistry and Applications (2000), Springer, New York p. 3
15. Elsaesser A., and Sundermeyer W. Tetrahedron Lett. 24 (1983) 2141-2142
16. Liu Y., Xu D., Xu Z., and Zhang Y. Synlett (2007) 1671-1674
17. Tanaka H., Yamashita S., Hamatani T., Ikemoto Y., and Torii S. Synth. Commun. 17 (1987) 789-794
18. Tanaka H., Yamashita S., Katayama Y., and Torii S. Chem. Lett. (1986) 2043-2044
19. Tanaka H., Yamashita S., and Torii S. Bull. Chem. Soc. Jpn. 60 (1987) 1951-1953
20. Tanaka H., Yamashita S., Yamanoue M., and Torii S. J. Org. Chem. (1989) 444-450
21. Josten R., and Ruppert I. J. Organomet. Chem. 329 (1987) 313-318
22. Beckers H., Buerger H., Bursch P., and Ruppert I. J. Organomet. Chem. 316 (1986) 41-50
23. Postovoi S.A., Kagramanova E.M., Mysov E.I., and Zeifman Y.V. Izv. Akad. Nauk. Ser. Khim. (1996) 1496-1498
24. Zeifman Y.V. Izv. Akad. Nauk. Ser. Khim. (1992) 464-468
25. Zeifman Y.V., Postovoi S.A., and German L.S. Izv. Akad. Nauk. SSSR, Ser. Khim. (1991) 2159-2160
26. Zeifman Y.V., and Postovoi S.A. J. Fluorine Chem. 125 (2004) 1815-1819
27. Postovoi S.A., Vol'pin I.M., Mysov E.I., Ziefman Y.V., and German L.S. Izv. Akad. Nauk. SSSR, Ser. Khim. (1989) 1173-1176
28. Zeifman Y.V., Postovoi S.A., Vol'pin I.M., and German L.S. Dokl. Akad. Nauk. SSSR 307 (1989) 1385-1390
29. Kurbakova A.P., Leites L.A., German L.S., and Kurykin M.A. J. Fluorine Chem. 77 (1996) 169-174
30. Hosokawa T., Matsumura A., Katagiri T., and Uneyama K. J. Org. Chem. 73 (2008) 1468-1474
31. Prakash G.K.S., and Hu J. Acc. Chem. Res. 40 (2007) 921-930
32. Ni C., and Hu J. Tetrahedron Lett. 46 (2005) 8273-8277
33. Prakash G.K.S., Wang Y., Hu J., and Olah G.A. J. Fluorine Chem. 126 (2005) 1361-1367
34. Petrov V., and Marshall W. J. Fluorine Chem. 128 (2007) 729-735
35. Burger K., Fuchs A., Hennig L., and Helmreich B. Tetrahedron Lett. 42 (2001) 1657-1659
36. Burger K., Fuchs A., Hennig L., Helmreich B., and Greif D. Monatsh. Chem. 132 (2001) 929-945
37. Burger K., Hennig L., Fuchs A., Greif D., Spengler J., and Albericio F. Monatsh. Chem. 136 (2005) 1763-1779
38. Sizov A.Y., Kovregin A.N., Serdyuk R.N., Vorob'ev M.V., Porosyatnikov V.A., Tsvetkov A.A., Korneev D.O., and Ermolov A.F. Izv. Akad. Nauk. SSSR (2006) 1156-1163
39. G. Sheldrick (Ed.), SHELXTL Sofware Suite, v. 6.0, Bruker Axes Corp., Madison, WI, 1996.