Trifluoromethylthiolation of N,O-bis-(trimethylsilyl)acetamide

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 178, Issue 1, 2003, Pages 107-113

  Munavalli, S ^a   Rohrbaugh, D K ^b   Rossman, D I ^b   Wagner, W G ^b   Durst, H D ^b  

^a SCIENCE APPLICATIONS INTERNATIONAL CORPORATION   (United States)

^b EDGEWOOD CHEMICAL BIOLOGICAL CENTER   (United States)

Author keywords

Mon and bis thiolated products; NMR and mass spectra; Silylacetamide; Trifluoromethylthiolation

Indexed keywords

ACETAMIDE DERIVATIVE; N,O BIS(TRIMETHYLSILYL)ACETAMIDE; SULFENIC ACID DERIVATIVE; TRIFLUOROMETHYLSULFENYLCHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0037249408     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500307779     Document Type: Article

References (73)

1. a) N. S. Simpson and P. A. Bartlett, Biochemistry, 30, 2255 (1991);
2. b) M. A. McClinton and D. A. McClinton, Tetrahedron, 48, 655 (1992);
3. c) J. T. Welch and S. Eshwarkrishnan (Wiley and Sons, New York, 1991);
4. d) M. R. C. Gerstenberger and A. Haas, Angew. Chem. Int. Ed., 20, 647 (1981);
5. e) R. Filler, J. Fluorine Chem., 33, 361 (1986);
6. f) R. Filler and Y. Kobayashi (Eds.), Biomedical Aspects of Fluorine Chemistry (Elsevier Publishers, New York, 1982);
7. g) J. T. Welch, Tetrahedron, 43, 3123 (1987);
8. h) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and L. Buettner, J. Fluorine Chem., 65, 15 (1993);
9. i) K. W. Pankiewicz and K. A. Watanabe, J. Fluorine Chem., 64, 15 (1993);
10. j) C. Wakselman, M. Tardeux, J.-L. Clevel, and B. Langlois, J. Chem. Soc., Chem. Comm., 993 (1991).
11. a) J. J. Lagowski, Quart. Rev., 233 (1959);
12. b) A. Haas, Pure Appl. Chem., 63, 1577 (1991).
13. a) T. Fujita, Prog. in Phys. Org. Chem., 14, 75 (1983);
14. b) A.-J. Beaumont and J. M. Clark, J. Fluorine Chem., 52, 295 (1991).
15. N. Muller, J. Pharm. Sci., 75, 987 (1986).
16. a) R. E. Banks, B. E. Smart, and J. C. Tatlow (Eds.), Organofluorine Chemistry, Principles and Commercial Applications (Plenum Press, New York, 1994);
17. b) R. Filler and Y. Kobayashi, Biomedical Aspects of Fluorine Chemistry (Elsevier, New York, 1993);
18. c) B. E. Smart (Ed.), Chem. Rev., 96, 1757 (1996).
19. a) G. E. Carr, R. D. Chambers, T. F. Holmes, and D. G. Parker, J. Chem. Soc., Perkin Trans., 1, 921 (1988);
20. b) Y. Kobayashi and I. Kumadaki, J. Chem. Soc., Perkin Trans., 1, 661 (1980);
21. c) J. Leroy, M. Rubinstein, and C. Wakselman, J. Fluorine Chem., 27, 291 (1985);
22. d) F. H. Mann, D. D. Coffman, and E. L. Muettertiess, J. Am. Chem. Soc., 81, 3575 (1959).
23. T. Umemoto, Y. Kuriu, S. Nakayama, and O. Miyano, Tetrahedron Lett., 1471 (1982).
24. a) S. Munavalli, D. I. Rossman, L. L. Szafraniec, W. T. Beaudry, D. K. Rohrbaugh, C. P. Ferrguson, and M. Gratzel, J. Fluorine Chem., 73, 1 (1995);
25. b) S. Sekiya and N. Ishikawa, Chem. Lett., 81 (1977).
26. T. Umemoto, Y. Kuriu, and S. Nakayama, Tetrahedron Lett., 3579 (1982).
27. D. J. Burton and Z.-Y. Yang, Tetrahedron, 48, 189 (1992).
28. S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and H. D. Durst, J. Fluorine Chem., 76, 7 (1996).
29. a) T. Katazume, J. Fluorine Chem., 22, 585 (1983);
30. b) T. Katazume and N. Ishikawa, J. Am. Chem. Soc., 107, 5186 (1985).
31. S. Rozen and R. Filler, Tetrahedron, 41, 1111 (1985).
32. a) P. Bravo and R. G. Resnati, Tetrahedron Asymmetry, 1, 661 (1990);
33. b) T. Yamazaki, J. T. Welch, and J.-S. Plummer, Tetrahedron, 41, 1111 (1985).
34. a) G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968);
35. b) G. G. Furin, O. A. Vyazankina, B. A. Gostevsky, and N. S. Vyazankin, Tetrahedron, 44, 2675 (1988);
36. c) M. Lalonde and T. H. Chan, Synthesis, 817 (1985);
37. d) P. Brownbridge, Synthesis, 1 (1983).
38. E. Block, M. Gerron, H. Kang, S. Liu, and J. Zubieta, J. Chem. Soc., Chem. Comm., 1031 (1988).
39. a) B. M. Trost, Chem. Rev., 78, 363 (1978);
40. b) I. Peterson and I. Fleming, Tetrahedron Lett., 993 and 2179 (1979);
41. c) B. M. Trost and D. P. Curran, J. Am. Chem. Soc., 102, 5699 (1980);
42. d) N. Ono, H. Miyaki, and A. Kaji, Synthesis, 1003 (1981).
43. a) S. Munavalli and D. I. Rossman, U.S. Pat. (1994);
44. b) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and L. Buettner, J. Fluorine Chem., 65, 15 (1993).
45. a) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, and C. P. Ferguson, J. Fluorine Chem., 60, 85 (1995);
46. b) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and L. J. Szafraniec, J. Fluorine Chem., 59, 91 (1992);
47. c) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, and C. P. Ferguson, J. Fluorine Chem., 61, 147 (1993);
48. d) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, and C. P. Ferguson, J. Fluorine Chem., 60, 155 (1993);
49. e) S. Munavalli, A. J. Muller, D. I. Rossman, D. K. Rohrbaugh, and C. P. Ferguson, J. Fluorine Chem., 63, 253 (1983);
50. f) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and H. D. Durst, J. Fluorine Chem., 79, 7 (1996);
51. g) S. Munavalli, G. W. Wagner, A. Bashir Hashemi, D. K. Rohrbaugh, and H. D. Durst, Syn. Comm., 27, 2847 (1997);
52. h) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and L. C. Buettner, J. Fluorine Chem., 65, 5 (1993);
53. i) S. Munavalli, A. Hassner, D. I. Rossman, S. Singh, D. K. Rohrbaugh, and C. P. Ferguson, J. Fluorine Chem., 73, 7 (1995);
54. j) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and H. D. Durst, J. Fluorine Chem., 83, 7 (1996);
55. k) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, and H. D. Durst, J. Fluorine Chem., 89, 189 (1998);
56. l) S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, L. R. McMahon, and H. D. Durst, J. Organometal. Chem., 587, 160 (1999).
57. L. M. Yagupolskii, N. V. Kondratenko, and V. P. Sambur, Synthesis, 721 (1975).
58. a) S. Munavalli, D. I. Rossman, D. K. Rohrbaugh, C. P. Ferguson, and F.-L. Hsu, Heteroatom. Chem., 3, 189 (1992);
59. b) A. L. Rheingold, S. Munavalli, D. I. Rossman, and C. P. Ferguson, Inorg. Chem., 33, 1723 (1994).
60. a) L. Blanko, P. Aice, and J. M. Conia, Synthesis, 194 (1976);
61. b) C. Girard and J. M. Conia, Tetrahedron Lett., 2327 (1974);
62. c) G. M. Rubottom, J. M. Gruber, and K. Kincaid, Synth. Comm., 6, 59 (1976).
63. a) M. Asaoka, N. Yanagida, K. Ishibashi, and H. Takai, Tetrahedron Lett., 22, 4269 (1981);
64. b) S. Kobayashi and I. Hachiya, Tetrahedron Lett., 33, 1625 (1992).
65. a) M. Bellassoued, N. Lensen, M. Bakasse, and S. Mouelhi, J. Org. Chem., 63, 8785 (1988);
66. b) N. Lensen, S. Mouelhi, and M. Bellassoued, Synth. Comm., 31, 1007 (2001).
67. B. M. Trost and Y. Tanigawa, J. Am. Chem. Soc., 101, 4413 (1979).
68. M. T. Reetz and A. Giannis, Synth. Comm., 11, 315 (1981).
69. S. T. Purrington and W. A. Jones, J. Fluorine Chem., 26, 43 (1983);
70. b) R. D. Chambers and J. Hutchinson, J. Fluorine Chem., 89, 229 (1998).
71. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, F. J. Berg, W. W. Wagner, and H. D. Durst, Synth. Comm., 30, 2854 (2000).
72. J. Fossey, D. Lefort, and J. Sorba, Free Radicals in Organic Chemistry (Wiley and Sons, New York, 1995).
73. a) H. Budzikiewicz, C. Djetassi, and D. H. Williams, Mass Spectra of Oraganic Compounds, (Holden-Day Publishers, San Francisco, 1967).