Generation of nitroalkanes, hydroximoyl halides and nitrile oxides from the reactions of β-nitrostyrenes with Grignard or organolithium reagents

Tetrahedron

Volumn 54, Issue 5-6, 1998, Pages 791-822

  Yao, Ching Fa ^a   Kao, Kuo Hsi ^a   Liu, Ju Tsung ^a   Chu, Cheng Ming ^a   Wang, Yeh ^a   Chen, Wen Chang ^a   Lin, Yu Mei ^a   Lin, Wen Wei ^a   Yan, Ming Chung ^a   Liu, Jing Yuan ^a   Chuang, Ming Ching ^a   Shiue, Jin Lien ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; NITRILE; NITROALKANE; ORGANOLITHIUM COMPOUND; STYRENE DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032576787     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10356-8     Document Type: Article

References (55)

1. (1) (a) Corey, E. J.; Estreicher, H, J. Am. Chem. Soc. 1978, 100, 6294.
2. (b) Seebach, D.; Colvin, E. W.; Weller, T. Chimia 1979, 33, 1.
3. (c) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
4. (d) Rosini, G.; Ballini, R. Synthesis 1988, 833.
5. (e) Barrett, A. Chem. Soc. Rev. 1991, 20, 95.
6. (2) (a) Bedford, C. D.; Nielsen, A. T. J. Org. Chem. 1978, 43, 2460.
7. (b) Hayama, T.; Tomoda, S.; Takeuchi, Y.; Nomura, Y. Tetrahedron Lett. 1983, 24, 2795.
8. (c) Seebach, D.; Knochel, P. Helv. Chim. Acta 1984, 67, 261.
9. (d) Seebach, D.; Giorgio, C.; Knochel, P. Tetrahedron 1985, 41, 4861.
10. (3) (a) Buckley, G. D. J. Chem. Soc. 1947, 1494.
11. (b) Buckley, G. D.; Ellery, E. J. J. Chem. Soc. 1947, 1497.
12. (c) Ashwood, M. S.; Bell, L. A.; Houghton, P. G.; Wright, S. H. B. Synthesies 1988, 379.
13. (4) Michel, J.; Henry-Basch, E. C. R. Acad. Sci. Ser. C 1966, 262, 1274.
14. (5) Langer, W.; Seebach, D. Helv. Chim. Acta 1979, 62, 1710.
15. (6) (a) Pecunioso, A.; Menicagli, R. Tetrahedron. 1987, 43, 5411.
16. (b)Pecunioso, A.; Menicagli, R. J. Org. Chem. 1988, 53, 45.
17. (c) Pecunioso, A.; Menicagli, R. J. Org. Chem. 1988, 53, 2614.
18. (d) Pecunioso, A.; Menicagli, R. J. Org. Chem. 1989, 54, 2391.
19. (7) (a) Hanson, A.-T.; Nillson, AM. Tetrahedron 1982, 38, 389.
20. (b) Stiver, S.; Yates, P. J. Chem. Soc., Chem. Commun. 1983, 50.
21. (c) Retherford, C.; Yeh, M.-C. P.; Schipor, I.; Chen, H. G.; Knochel, P. J. Org. Chem. 1989, 54, 5200.
22. (d) Retherford, C.; Knochel, P. Tetrahedron Lett. 1991, 32, 441.
23. (e) Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5425.
24. (f) Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5431.
25. (8) Picnnic, H. W. Org. React. 1990, 38, 655.
26. (9) Edward, J. T.; Tremaine, P. H. Can, J. Chem. 1971, 3483, 3489, 3493 and references cited therein.
27. (10) (a) Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
28. (b) Christl, M.; Huisgen, R. Chem. Ber. 1973, 106, 3345.
29. (c).Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron. Lett. 1997, 38, 1547.
30. (d) Knight, J.; Parson, P. J. J. Chem. Soc., Chem. Commun. 1987, 189.
31. (e) Nishiyama, H.; Arai, H.; Okhi, T.; Itoh, K. J. Am. Chem. Soc. 1985, 107, 5310.
32. (f) Curran, D. P.; Fenk, C. J. Tetrahedron. Lett. 1986, 27, 486.
33. (11) (a) Chiang, Y. H. J. Org. Chem. 1971, 36, 2146.
34. (b) Peake, C. J.; Strickland, J. H. Synth. Commum. 1986, 16, 763.
35. (c) Rheinboldt, H. Liebigs Ann. Chem. 1927, 451, 161.
36. (d) Liu, K. C.; Shelton, B. R.; Howe, R.K. J. Org. Chem. 1980, 45, 3916.
37. (e) Kim, J. N.; Ryu, E. K. Org. Chem. 1992, 57, 6649.
38. (f) Kumaran, G.; Kulkarni, G. H. J. Org. Chem. 1997, 62, 1516.
39. (12) Yao, C.-F.; Chen, W.-C.; Lin, Y.-M. Tetrahedron Lett. 1996, 37, 6339.
40. (13) Torsell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis 1988, VCH, New York.
41. (14) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed. Wiley-Interscience; New York, 1984, Vol. 2.
42. (b) Curran, D.P. Advances in Cycloaddition; JAI Press; Greenwich, CT, 1988, p 129.
43. (15) Jung, M. E.; VU. B. T. Tetrahedron Lett. 1996, 37, 451.
44. (16) (a) Gottlieb, L.; Hassner, A. J. Org. Chem. 1995, 60, 3759.
45. (b) Namboothiri, I. N. N.; Hassner, A. Gottlieb, H. E. J. Org. Chem. 1997, 62, 485.
46. (17) (a) Henry, G.; Moore, F. W.; Baine, O. J. Am. Chem. Soc. 1941, 63, 2479.
47. (b) Corey, E. J.; Balanson, R. D. J. Am. Chem. Soc. 1974, 96, 6517.
48. (18) Bordwell, F. G.; Garbisch, E. W. J. Org. Chem. 1962, 27, 2322, 3049.
49. (19) Russell, G. A.; Dedolph, D. J. Org. Chem. 1985, 50, 3878.
50. (20) Bouveault, L; Wahl, A. C. R. Acad. Sci. 1902, 135, 41.
51. (21) Hurtric, C.; Kumler, W. D. J. Am. Chem. Soc. 1956, 78, 618.
52. (22) Fischer, E.; Hagen, J.; Jung, R.; Knies, W.; Kohl, C.; Listmannk, F.; Neugebauer, W.; Schulte, T. Ber. 1922, 18, 1835.
53. (23) Namboothiri, I. N. N.; Hassner, A. J. Organomet. Chem. 1996, 518, 69.
54. (24) Ohta, H.; Ozaki, K.; Tsuchihashi, G.-i Chem. Lett. 1987,191.
55. (25) Ohta, H.; Kobayashi, N.; Ozakim K. J. Org. Chem. 1989, 54, 1802.