Oxidative Generation of 1-Nitroalkyl Radicals and Their Addition Reaction to Olefins

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 10, 1997, Pages 2525-2534

  Arai, Noriyoshi ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001697893     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.2525     Document Type: Article

References (32)

1. B. Giese, "Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds," Pergamon, Oxford (1986).
2. D. P. Curran, Synthesis, 1988, 417 and 489.
3. P. Renaud and M. A. Fox, J. Org. Chem., 53, 3745 (1988).
4. D. Willemin and A. B. Alloum, Synth. Commun., 22, 3169 (1992).
5. T. Cohen, K. McNamara, M. A. Kuzemko, K. Ramig, J. J. Landi, Jr., and Y. Dong, Tetrahedron, 49, 7931 (1993).
6. A. S. Kende, K. Koch, and C. A. Smith, J. Am. Chem. Soc., 110, 2210 (1988).
7. J. L. Morgat and R. Palloud, C. R. Hebd. Séances Acad. Sci., 260, 5579 (1965).
8. H. J. Schäfer, Angew. Chem., Int. Ed. Engl., 20, 911 (1981); H. Schäfer and A. Al Azrak, Chem. Ber., 105, 2398 (1972).
9. H. J. Schäfer, Angew. Chem., Int. Ed. Engl., 20, 911 (1981); H. Schäfer and A. Al Azrak, Chem. Ber., 105, 2398 (1972).
10. N. Arai and K. Narasaka, Chem. Lett., 1995, 987.
11. W. R. Bowman and S. W. Jackson, Tetrahedron Lett., 30, 1857 (1989).
12. K. Narasaka, K. Iwakura, and T. Okauchi, Chem. Lett., 1991, 423.
13. M. E. Kurz, P. Ngoviwatchai, and T. Tantrarant, J. Org. Chem., 46, 4668 (1981); M. E. Kurz and P. Ngoviwatchai, J. Org. Chem., 46, 4672 (1981).
14. M. E. Kurz, P. Ngoviwatchai, and T. Tantrarant, J. Org. Chem., 46, 4668 (1981); M. E. Kurz and P. Ngoviwatchai, J. Org. Chem., 46, 4672 (1981).
15. N. Kornblum, H. K. Singh, and W. J. Kelly, J. Org. Chem., 48, 332 (1983).
16. A. S. Kende and K. Koch, Tetrahedron Lett., 27, 6051 (1986).
17. W. R. Bowman, D. S. Brown, C. A. Burns, and D. Crosby, J. Chem. Soc., Perkin Trans, 1, 1993, 2099.
18. M. Montavon, H. Lindlar, R. Marbet, R. Rüegg, G. Ryser, G. Saucy, P. Zeller, and O. Isler, Helv. Chim. Acta, 40, 1250 (1957).
19. D. Seebach and F. Lehr, Angew. Chem., Int. Ed. Engl., 15, 505 (1976).
20. M. V. Proštenik and I. Butula, Angew. Chem., Int. Ed. Engl., 21, 139 (1976).
21. The chemical shift of 4g showed good agreement with the literature: T. Jeffery-Luong and G. Linstrumelle, Synthesis, 1982, 738.
22. w = 0.050, 3790 unique reflections. The structure was solved by direct method (Fan Hai-Fu, "SAPI91," "Structure Analysis Programs with Intelligent Control," Rigaku Corporation, Tokyo, Japan) and expanded using Fourier technique (P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, and C. Smykalla, "DIRDIF92," "The DIRDIF Program System," Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands). The lists of atomic coordinates, anisotropic parameters for non-hydrogen atoms, and the ORTEP drawing are deposited as Document No. 70039 at the Office of the Editor of Bull. Chem. Soc. Jpn.
23. The calculation was carried out with MacroModel ver.5.5 using MM2* force field: F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, and W. C. Still, J. Comput. Chem., 11, 440 (1990).
24. J. Fossey, D. Lefort, and J. Sorba, "Free Radicals in Organic Chemistry," John Wiley & Sons, New York (1995).
25. D. N. Hendrickson, Y. S. Sohn, and H. B. Gray, Inorg. Chem., 10, 1559 (1971).
26. M. M. Ray, J. N. Adhya, D. Biswas, and S. N. Podder, Aust. J. Chem., 19, 1737 (1966).
27. T. G. Clarke, N. A. Hampson, J. B. Lee, J. R. Morley, and B. Seanlan, Can. J. Chem., 47, 1649 (1969).
28. H. Sano, M. Okawara, and Y. Ueno, Synthesis, 1984, 933.
29. E. P. Kohler and H. M. Chadwell, Org. Synth., Coll. Vol. 1, 78 (1941).
30. T. Miyakoshi and S. Saito, Nippon Kagaku Kaishi, 1984, 458; T. Miyakoshi, S. Saito, and J. Kumanotani, Chem. Lett., 1981, 1677.
31. T. Miyakoshi and S. Saito, Nippon Kagaku Kaishi, 1984, 458; T. Miyakoshi, S. Saito, and J. Kumanotani, Chem. Lett., 1981, 1677.
32. G. Rosini, R. Ballini, and P. Sorrenti, Tetrahedron, 39, 4127 (1983).