Sulfinatodehalogenation reactions of gem-aryl disubstituted methylenecyclopropanes with perfluoroiodoalkanes

Journal of Fluorine Chemistry

Volumn 126, Issue 5, 2005, Pages 809-817

  Shi, Min ^a   Huang, Jin Wen ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Cyclopropyl radical; Perfluoroiodoalkanes; Radical transformation; Ring opening reaction of MCPs; Sodium dithionite; Sulfinatodehalogenation

Indexed keywords

EID: 18644385141     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.03.007     Document Type: Article

References (71)

1. A. Brandi, and A. Goti Chem. Rev. 98 1998 589 635
2. A. de Meijere Carbocyclic Three-Membered Ring Compounds, in Houben-Weyl E 17a-c 1996 Thieme Stuttgart
3. For a recent review I. Nakamura, and Y. Yamamoto Adv. Synth. Catal. 344 2002 111 129
4. D.H. Camacho, I. Nakamura, S. Saito, and Y. Yamamoto Angew. Chem. Int. Ed. Engl. 38 1999 3365 3367
5. D.H. Camacho, I. Nakamura, S. Saito, and Y. Yamamoto J. Org. Chem. 66 2001 270 275
6. I. Nakamura, H. Itagaki, and Y. Yamamoto J. Org. Chem. 63 1998 6458 6459
7. H. Nüske, M. Notlemeyer, and A. de Meijere Angew. Chem. Int. Ed. Engl. 40 2001 3411 3413
8. S. Bräse, and A. de Meijere Angew. Chem. Int., Ed. Engl. 34 1995 2545 2547
9. N. Tsukada, A. Shibuya, I. Nakamura, and Y. Yamamoto J. Am. Chem. Soc. 119 1997 8123 8124
10. Y. Inoue, T. Hibi, H. Sataka, and H. Hashimoto Chem. Comm. 1979 982 983
11. P. Binger, and A. Germer Chem. Ber. 114 1981 3325 3335
12. I. Nakamura, B.H. Oh, S. Saito, and Y. Yamamoto Angew. Chem. Int., Ed. Engl. 40 2001 1298 1300
13. B.H. Oh, I. Nakamura, S. Saito, and Y. Yamamoto Tetrahedron Lett. 42 2001 6203 6205
14. A.G. Bessmertnykh, K.A. Blinov, Y.K. Grishin, N.A. Donskaya, E.V. Tveritinova, N.M. Yur'eva, and I.P. Beletskaya J. Org. Chem. 62 1997 6069 6076
15. M. Lautens, C. Meyer, and A. Lorenz J. Am. Chem. Soc. 118 1996 10676 10677
16. T. Ishiyama, S. Momota, and N. Miyaura Synlett 1999 1790 1792
17. M. Suginome, T. Matsuda, and Y. Ito J. Am. Chem. Soc. 122 2000 11015 11016
18. N. Chatani, H. Takaya, and T. Hanafusa Tetrahedron Lett. 29 1988 3979 3982
19. M. Lautens, W. Klute, and W. Tam Chem. Rev. 96 1996 49 92
20. T. Ohta, and H. Takaya B.M. Trost I. Fleming L.A. Paquette Comprehensive Organic Chemistry 5 1991 Pergamon Press Oxford pp. 1185-1196
21. P. Binger, and T. Schmidt A. de Meijere Methods of Organic Chemistry (Houben-Weyl) E 17c 1997 Thieme Stuttgart pp. 2217-2294
22. P. Binger, and H.M. Buch Top. Curr. Chem. 135 1987 77 151
23. M.W. Nötzel, K. Rauch, T. Labahn, and A. de Meijere Org. Lett. 4 2002 839 841
24. D. Takauchi, and K. Dsakada Chem. Commun. 2002 646 647
25. A. de Meijere, A. Leonov, T. Heiner, M. Noltemeyer, and M.T. Bes Eur. J. Org. Chem. 2003 472 478
26. V.N. Belov, A.I. Savchenko, V.V. Sokolov, A. Straub, and A. de Meijere Eur. J. Org. Chem. 2003 551 561
27. A. de Meijere, I.D. Kuchuk, V.V. Sokolov, T. Labahn, K. Rauch, M. Es-Sayed, and T. Krämer Eur. J. Org. Chem. 2003 985 997
28. A.I. Siriwardana, I. Nakamura, and Y. Yamamoto Tetrahedron Lett. 44 2003 4547 4550
29. M. Shi, L.-X. Shao, and B. Xu Org. Lett. 5 2003 579 582
30. L.-X. Shao, and M. Shi Adv. Synth. Catal. 345 2003 963 966
31. A. Brandi, S. Cicchi, F.M. Cordero, and A. Goti Chem. Rev. 103 2003 1213 1269
32. A.I. Siriwardana, I. Nakamura, and Y. Yamamoto Tetrahedron Lett. 44 2003 985 990
33. M. Shi, and B. Xu Org. Lett. 4 2002 2145 2148
34. M. Shi, Y. Chen, B. Xu, and J. Tang Tetrahedron Lett. 43 2002 8019 8024
35. G.L.N. Peron, J. Kitteringham, and J.D. Kilburn Tetrahedron Lett. 41 2000 1615 1618
36. G.L.N. Peron, D. Norton, J. Kitteringham, and J.D. Kilburn Tetrahedron Lett. 42 2001 347 349
37. L. Patient, M.B. Berry, and J.D. Kilburn Tetrahedron Lett. 44 2003 1015 1017
38. B. Xu, and M. Shi Org. Lett. 5 2003 1415 1418
39. L.-X. Shao, and M. Shi Eur. J. Org. Chem. 2004 426 430
40. A.T. Bottini, and L.I. Cabral Tetrahedron 34 1978 3187 3194
41. S. Kozhushkov, T. Spätch, T. Fiebig, B. Galland, M.-F. Ruasse, P. Xavier, Y. Apeloig, and A. de Meijere J. Org. Chem. 68 2002 4100 4114 and references cited therein
42. I. Nakamura, M. Kamada, and Y. Yamamoto Tetrahedron Lett. 45 2004 2903 2906
43. N. Legrand, B. Quiclet-Sire, and S.Z. Zard Tetrahedron Lett. 41 2000 9815 9818
44. D. Destabel, J.D. Kilburn, and J. Knight Tetrahedron 50 1994 11267 11288
45. R.J. Boffey, M. Santagostino, J.D. Kilburn, and W.G. Whittingham Chem. Commun. 1998 1875 1876
46. R.J. Boffey, W.G. Whittingham, and J.D. Kilburn J. Chem. Soc., Perkin Trans. 1 2001 487 496
47. S.I. Kozhushkov, M. Brandl, and A. de Meijere Eur. J. Org. Chem. 1998 1535 1542
48. B. Xu, Y. Chen, and M. Shi Tetrahedron Lett. 43 2002 2781 2784
49. H.J.P. De Lijser, T.S. Cameron, and D.R. Arnold Can. J. Chem. 75 1997 1795 1809
50. F.-H. Wu, B.-N. Huang, and W.-Y. Huang Youjihuaxue 13 1993 449 459
51. F.-H. Wu, and W.-Y. Huang Youjihuaxue 17 1997 106 125
52. W.-Y. Huang, B.-N. Huang, and C.-M. Hu J. Fluoro. Chem. 23 1983 193 204
53. T. Ozawa, M. Setaka, and T. Kwan Bull. Chem. Soc. Jpn. 44 1971 3473 3474
54. M. Tordeux, B. Langlois, and C. Wakselman J. Org. Chem. 54 1989 2353 2357
55. D.J. Burton, A.S. Modak, R. Guneratne, D.B. Su, W.B. Cen, R.L. Kirchmeier, and J.M. Shreeve J. Am. Chem. Soc. 111 1989 1773 1776
56. W.-Y. Huang J. Fluoro. Chem. 58 1992 1 8
57. D.J. Burton, and L.J. Hehoe J. Org. Chem. 35 1970 1339 1342
58. M. Corallo, and Y. Pietrasanta Tetrahedron 32 1976 2295 2301
59. O. Gandolfi, and M. Cais J. Organomet. Chem. 125 1977 141 154
60. J. Elzinga, and M. Hogeveen J. Org. Chem. 45 1980 3957 3969
61. T. Tsuji, and H. Nagashima Tetrahedron 41 1985 393 397
62. R. Grigg, J. Delvin, S.R.M. Ramusuddu, and D.J. Stevenson J. Chem. Soc., Perkin Trans. 1 1987 1515 1520
63. K. Nohair, I. Lachaise, J.P. Daugam, and J.Y. Nedelec Tetrahedron Lett. 33 1992 213 216
64. D.P. Curran Synthesis 1988 417 439
65. 000 = 4428; diffractometer: Rigaku AFC7R; Residuals: R; Rw: 0.0730, 0.1899. CCDC-218141 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk ].
66. J.K. Kochi, P.J. Krusic, and D.R. Eaton J. Am. Soc. Chem. 91 1969 1877 1879
67. L. Mathew, and J. Warkentin J. Am. Soc. Chem. 108 1986 7981 7984
68. V.W. Bowry, J. Lusztyk, and K.U. Ingold J. Am. Soc. Chem. 113 1991 5687 5698
69. A.L.J. Beckwith, and V.W. Bowry J. Am. Soc. Chem. 116 1994 2710 2716
70. J. Masnovi, E.G. Samsel, and R.M. Bullock Chem. Commun. 1989 1044 1045
71. K. Utimoto, M. Tamura, and K. Sisido Tetrahedron 14 1973 1169 1171