Phototrifluoromethylsulfenylation of phenylcyclopropane

Journal of Fluorine Chemistry

Volumn 89, Issue 2, 1998, Pages 189-194

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

^a SCIENCE APPLICATIONS INTERNATIONAL CORPORATION   (United States)

^b U S ARMY   (United States)

Author keywords

Cyclopropane; Photolysis; Trifluoromethylsulfenyl

Indexed keywords

EID: 0032577157     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(98)00136-5     Document Type: Article

References (54)

1. [1] Z. Rappoport (Ed.), The Chemistry of the Cyclopropyl Group, Wiley, New York, 1987.
2. [2] A. Greenberg, J.F. Liebman, Strained Organic Molecules, Academic Press, New York, 1978.
3. [3] H.N.C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J.M. Tanko, T. Hudlicky, Chem. Rev. 89 (1989) 165.
4. [4] J.F. Liebman, A. Greenberg, Chem. Rev. 89 (1989) 1225.
5. [5] M. Ramaiah, Synthesis (1984) 529.
6. [6] C.A. Deakyne, L.C. Allen, V.W. Laurie, J. Am. Chem. Soc. 99 (1977) 1343.
7. [7] J.A. Dill, A. Greenberg, J.F. Liebman, J. Am. Chem. Soc. 101 (1979) 6814.
8. [8] W.R. Dolbier Jr., Ace. Chem. Res. 14 (1981) 195.
9. [9] B.E. Smart, in: J.F. Liebman, A. Greenberg (Eds.), Molecular Structure and Energetics, Vol. 3, VCH Publishers, Deerfield Beach, FL, 1986.
10. [10] J.F. Liebman, W.R. Dolbier Jr., A. Greenberg Jr., J. Phys. Chem. 90 (1986) 384.
11. [11] S. Inagaki, Y. Ishitani, T. Kakefu, J. Am. Chem. Soc. 116 (1994) 5954.
12. [12] Z.-Y. Yang, P.J. Krusic, B.E. Smart, J. Am. Chem. Soc. 117 (1995) 5397.
13. [13] J.M. Tanko, R.H. Mas, N.K. Suleman, J. Am. Chem. Soc. 112 (1990) 5557.
14. [14] R.E. Drumright, R.H. Mas, J.S. Merola, J.M. Tanko, J. Org. Chem. 55 (1990) 4098.
15. [15] J.M. Tanko, N.K. Suleman, J. Am. Chem. Soc. 116 (1992) 5162.
16. [16] J.M. Tanko, N.K. Suleman, G.A. Hulvey, A. Park, J.E. Powers, J. Am. Chem. Soc. 115 (1993) 4520.
17. [17] J.C. Traynham, Y.S. Lee, J. Am. Chem. Soc. 96 (1974) 3590.
18. [18] C. Walling, P.S. Frederick, J. Am. Chem. Soc. 84 (1962) 3326.
19. [19] C.J. Upton, J.H. Incremona, J. Org. Chem. 41 (1976) 523.
20. [20] G.G. Maynes, D.E. Applequist, J. Am. Chem. Soc. 95 (1973) 856.
21. [21] K.J. Shea, P.S. Skell, J. Am. Chem. Soc. 95 (1978) 6728.
22. [22] D.E. Applequist, L.F. McKenzie, J. Org. Chem. 41 (1976) 2262 and references cited therein.
23. [23] T. Hudlicky, T.M. Kutchan, S.M. Naqvi, Org. React. 33 (1985) 287.
24. [24] W. Adam, T. Oppenlaender, G. Zang, J. Org. Chem. 50 (1985) 3303.
25. [25] H.E. Zimmerman, R.W. Binkley, Tetrahedron Lett. 26 (1985) 5859.
26. [26] N.S. Zefirov, S.I. Kozhushkov, T.S. Kuzmnetsova, I.M. Sosonkin, Zh. Org. Khem. 22 (1986) 666.
27. [27] R.T. LaLonde, P.B. Ferraro, A.D. Debboli Jr., Org. J. Chem. 37 (1972) 1094.
28. [28] S. Munavalli, D.I. Rossman, A.J. Muller, H.S. Aaron, C.P. Ferguson, J.W. King, D.K. Rohrbaugh, L.C. Buettner, American Chemical Society 10th Winter Fluorine Conference, St. Petersburg, FL, 28 Jan-2 Feb 1991, Abstract No. 38.
29. [29] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, F.-L. Hsu, Heteroatom Chem. 3 (1992) 189.
30. [30] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, L.J. Szafraniec, J. Fluorine Chem. 59 (1992) 91.
31. [31] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson. L.C. Buettner, J. Fluorine Chem. 65 (1993) 15.
32. [32] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, 206th American Chemical Society National Meeting, Division of Fluorine Chemistry, Chicago, IL, 21-27 Aug 1993, Abstract No. 17.
33. [33] S. Munavalli, A. Hassner, D.I. Rossman, S. Singh, D.K. Rohrbaugh, C.P. Ferguson, J. Fluorine Chem. 73 (1995) 7.
34. [34] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, H.D. Durst, J. Fluorine Chem. 99 (1996) 7.
35. [35] S. Munavalli, G.W. Wagner, A. Bashir-Hashemi, D.K. Rohrbaugh, H.D. Durst, Synth. Commun. 27 (1997) 2847.
36. [36] R.N. Newman-Evans, R.J. Simon, B.K. Carpenter, J. Org. Chem. 55 (1990) 695.
37. [37] J.P. Chesick, J. Am. Chem. Soc. 82 (1960) 3277.
38. [38] R.N. Haszaldine, R. Rowland, J.G. Speight, A.E. Tipping, J. Chem. Soc., Perkin Trans. 1 (1980) 314 and references cited therein.
39. [39] J.A. Berson, L.D. Petersen, B.K. Carpenter, J. Am. Chem. Soc. 98 (1976) 122.
40. [40] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, H.D. Durst (under preparation).
41. [41] R.J. Cody, M.J. Dzvonik, S. Glicker, J. Chem. Phys. 82 (1985) 3100.
42. [42] B.B. Craig, W.L. Faust, J. Chem. Phys. 79 (1983) 1286.
43. [43] O. Hammerich, V.D. Parker, Adv. Phys. Org. Chem. 20 (1984) 55.
44. [44] A.K.M.M. Hoque, A.C. Kovlesky, W.K. Lee, H.J. Shine, Tetrahedron Lett. (1985) 5655.
45. [45] H.J. Shine, D.H. Bae, A.K.M.M. Hoque, A. Kajstura, W.K. Lee, R.W. Shah, M. Soroka, P.S. Engel, D.E. Keys, Phosphorus Sulfur 23 (1985) 111.
46. [46] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, H.D. Durst (manuscripts under preparation).
47. [47] S. Munavalli, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, H.D. Banks, J. Fluorine Chem. 60 (1993) 85.
48. [48] S. Munavalli, E.O. Lewis, A.J. Muller, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, J. Fluorine Chem. 63 (1993) 253.
49. [49] S. Munavalii, A.J. Muller, D.I. Rossman, D.K. Rohrbaugh, C.P. Ferguson, J. Fluorine Chem. 67 (1994) 37 and references cited therein.
50. [50] H. Budzikiewicz, C. Djerassi, D.H. Williams, Mass Spectrometry of Organic Compounds, Holden-Day, San Francisco, CA, 1967, p. 418.
51. [51] S.-T. Lin, M.-L. Lin, W.-C. Lin, Org. Mass Spectrom. 25 (1990) 667 and references cited therein.
52. [52] J.O. Lay, M.L. Cross, J.J. Zwinselman, N.M.M. Nibbering, Org. Mass Spectrom. 18 (1983) 16
53. [53] J.R. Collins, G.A. Gallup, J. Am. Chem. Soc. 104 (1982) 1531.
54. [54] C. Koppel, H. Schwartz, F. Bohlmann, Org. Mass Spectrom. 8 (1982) (1974) 25.