An efficient methodology for the C-C bond forming radical cyclization of hydrophobic substrates in water: Effect of additive on radical reaction in water

Tetrahedron

Volumn 59, Issue 1, 2003, Pages 77-85

  Nambu, Hisanori ^a   Anilkumar, Gopinathan ^a   Matsugi, Masato ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C bond; Cetyltrimethylammonium bromide; Radical reactions

Indexed keywords

1 ETHYLPIPERIDINE HYPOPHOSPHITE; 2,2' AZOBIS[2 (2 IMIDAZOLIN 2 YL)PROPANE]; CETRIMIDE; PHOSPHITE; PROPANE; SURFACTANT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; HYDROPHOBICITY; METHODOLOGY; PRIORITY JOURNAL; RADICAL REACTION;

EID: 0037213655     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01448-5     Document Type: Article

References (60)

1. (a) Li C.-J., Chan T.-H. Organic Reactions in Aqueous Media. 1997;Wiley, New York, (b) Grieco P.A. Organic Synthesis in Water. 1998;Blackie, London.
2. (a) Li C.-J., Chan T.-H. Organic Reactions in Aqueous Media. 1997;Wiley, New York, (b) Grieco P.A. Organic Synthesis in Water. 1998;Blackie, London.
3. (a) Rideout D.C., Breslow R. J. Am. Chem. Soc. 102:1980;7816
4. (b) Breslow R., Maitra U., Rideout D.C. Tetrahedron Lett. 24:1983;1901
5. (c) Breslow R. Acc. Chem. Res. 24:1991;159.
6. (a) Ponaras A.A. J. Org. Chem. 48:1983;3866
7. (b) Coates R.M., Roger B.D., Hobbs S.J., Peck D.R., Curran D.P. J. Am. Chem. Soc. 109:1987;1160
8. (c) Gajewski J.J., Jurayj J., Kimbrough D.R., Gande M.E., Ganem B., Carpenter B.K. J. Am. Chem. Soc. 109:1987;1170
9. (d) Copley S.D., Knowles J.R. J. Am. Chem. Soc. 109:1987;5008
10. (e) Brandes E.B., Grieco P.A., Gajewski J.J. J. Org. Chem. 54:1989;515.
11. (a) Li C.-J. Tetrahedron. 52:1996;5643
12. (b) Li C.-J., Chan T.-H. Tetrahedron. 55:1999;11149.
13. (a) Lubineau A. J. Org. Chem. 51:1986;2142
14. (b) Lubineau A., Meyer E. Tetrahedron. 44:1988;6065
15. (c) Kobayashi S., Hachiya I. J. Org. Chem. 59:1994;3590.
16. (a) Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds. 1986;Pergamon, Oxford,
17. (b) Curran D.P. Synthesis. 1988;489
18. (c) Motherwell W.B., Crich D. Free-Radical Reactions in Organic Synthesis. 1992;Academic, London,
19. (d) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237
20. (e) Molander G.A., Harris C.R. Chem. Rev. 96:1996;307
21. (f) Snider B.B. Chem. Rev. 96:1996;339
22. (g) Renaud P., Sibi M.P. Radicals in Organic Synthesis. 2001;Wiley-VCH, Weinheim.
23. (a) Light J., Breslow R. Tetrahedron Lett. 31:1990;2957
24. (b) Rai R., Collum D.B. Tetrahedron Lett. 35:1994;6221.
25. Yamazaki O., Togo H., Nogami G., Yokoyama M. Bull. Chem. Soc. Jpn. 70:1997;2519.
26. (a) Yorimitsu H., Nakamura T., Shinokubo H., Oshima K. J. Org. Chem. 63:1998;8604
27. (b) Wakabayashi K., Yorimitsu H., Shinokubo H., Oshima K. Bull. Chem. Soc. Jpn. 73:2000;2377
28. (c) Yorimitsu H., Nakamura T., Shinokubo H., Oshima K., Omoto K., Fujimoto H. J. Am. Chem. Soc. 122:2000;11041.
29. Yorimitsu H., Shinokubo H., Matsubara S., Oshima K. J. Org. Chem. 66:2001;7776.
30. (a) Miyabe H., Ueda M., Naito T. J. Org. Chem. 65:2000;5043
31. (b) Miyabe H., Ueda M., Nishimura A., Naito T. Org. Lett. 4:2002;131.
32. (a) Jang D.O., Cho D.H. Synlett. 2002;631
33. (b) Jang D.O., Cho D.H. Tetrahedron Lett. 43:2002;5921
34. (c) Jang D.O., Cho D.H. Synlett. 2002;1523
35. (d) Nambu H., Hata K., Matsugi M., Kita Y. Chem. Commun. 2002;1082.
36. Kita Y., Nambu H., Ramesh N.G., Anilkumar G., Matsugi M. Org. Lett. 3:2001;1157.
37. (a) Barton D.H.R., Jang D.O., Jaszberenyi J.C. Tetrahedron Lett. 33:1992;5709
38. (b) Barton D.H.R., Jang D.O., Jaszberenyi J.C. J. Org. Chem. 58:1993;6838
39. (c) Jang D.O. Tetrahedron Lett. 37:1996;5367
40. (d) Jang D.O., Cho D.H., Chung C.-M. Synlett. 2001;1923.
41. (a) Kita Y., Gotanda K., Fujimori C., Murata K., Wakayama R., Matsugi M. Tetrahedron Lett. 38:1997;3549
42. (b) Kita Y., Gotanda K., Murata K., Suemura M., Sano A., Yamaguchi T., Oka M., Matsugi M. Org. Process Res. Dev. 2:1998;250
43. (c) Kita Y., Gotanda K., Ohira C., Suemura M., Sano A., Matsugi M. J. Org. Chem. 64:1999;6928. and references cited therein.
44. Kita Y., Matsugi M. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Radicals in Organic Synthesis. Vol. 1:2001;1-10 Wiley-VCH, Weinheim. The water-soluble azo type radical initiators used in our studies are available from Wako Pure Chemical Industries, Ltd. Osaka, Japan.
45. (a) Breslow R., Maitra U. Tetrahedron Lett. 25:1984;1239
46. (b) Kool E.T., Breslow R. J. Am. Chem. Soc. 110:1988;1596
47. (c) Breslow R., Rizzo C.J. J. Am. Chem. Soc. 113:1991;4340.
48. (a) Fendler J.H. Catalysis in Micellar and Macromolecular Systems. 1998;Academic, New York,
49. (b) Tascioglu S. Tetrahedron. 52:1996;11113
50. (c) Tohma H., Takizawa S., Watanabe H., Kita Y. Tetrahedron Lett. 39:1998;4547
51. (d) Tohma H., Takizawa S., Watanabe H., Fukuoka Y., Maegawa T., Kita Y. J. Org. Chem. 64:1999;3519.
52. Maitra has already reported a radical reduction using surfactants and Sn compound in water Maitra U., Sarma K.D. Tetrahedron Lett. 35:1994;7861.
53. (a) Chatgilialoglu C. Acc. Chem. Res. 25:1992;188
54. (b) Baguley P.A., Walton J.C. Angew. Chem. Int. Ed. 37:1998;3072.
55. (a) Okabe M., Tada M. Bull. Chem. Soc. Jpn. 55:1982;1498
56. (b) Nakamura E., Machii D., Inubushi T. J. Am. Chem. Soc. 111:1989;6849.
57. Curran D.P., Totleben M.J. J. Am. Chem. Soc. 114:1992;6050.
58. Rawal V.H., Singh S.P., Dufour C., Michoud C. J. Org. Chem. 58:1993;7718.
59. (a) Ueno Y., Moriya O., Chino K., Watanabe M., Okawara M. J. Chem. Soc., Perkin Trans. 1. 1986;1351
60. (b) Tang J., Shinokubo H., Oshima K. Tetrahedron. 55:1999;1893.