One-pot synthesis of the hydroximoyl chlorides and [3.3.0] bicyclic compounds from the reactions of β-nitrostyrenes with stabilized nucleophiles

Tetrahedron

Volumn 54, Issue 46, 1998, Pages 13997-14014

  Kao, Kuo Hsi ^c   Yang, Cherng Shi ^c   Liu, Ju Tsung ^c   Lin, Wen Wei ^c   Fang, Hui Yu ^c   Yao, Ching Fa ^a   Chen, Kwunmin ^a,b  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^b CHAOYANG UNIVERSITY OF TECHNOLOGY   (Taiwan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

NITROALKANE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032512081     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00883-7     Document Type: Article

References (37)

1. 1. (a) Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
2. (b) Seebach, D.; Colvin, E. W.; Well, 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. G. M. Chem. Soc. Rev. 1991, 20, 95.
6. (e) Several articles in Tetrahedron: Symposia in Print 1990, 46 (21), Barrett, A. G. M. Ed.
7. 2. (a)Torsell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH; New York, 1988.
8. (b) Gottlieb, L.; Hassner, A. J. Org. Chem. 1995, 60, 3759.
9. (c) Dehaen, W.; Hassner, A. Tetrahedron Lett. 1990, 31, 743.
10. 3. (a) Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
11. (b) Hassner, A.; Basel, Y. Synthesis 1997, 309.
12. (c) Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547.
13. 4. (a) Kamaran, G.; Kulkarni, G. H. Tetrahedron Lett. 1994, 35, 5517.
14. (b) Kamaran, G.; Kulkarni, G. H. Tetrahedron Lett. 1994, 35, 9099.
15. (c) Kamaran, G.; Kulkarni, G. H. J. Org. Chem. 1997, 62, 1516.
16. 5. (a) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A.; Ed.; Wiley-Interscience; New York, 1984; Vol. 2.
17. (b) Curran, D. P. Advances in Cycloaddition; JAI Press; Greenwich , CT, 1988; p 129.
18. 6. (a) Hassner, A.; Maurya, R.; Padwa, A.; Bullock, W. H. J. Org. Chem. 1991, 56, 2775.
19. (b) Hassner, A.; Maurya, R.; Mesko, E. Tetrahedron Lett. 1988, 29, 5313.
20. (c) Hassner, A.; Maurya, R. Tetrahedron Lett. 1989, 30, 5803.
21. (d) Grigg, R. Chem. Soc. Rev. 1987, 16, 89.
22. (e) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron Lett. 1990, 31, 559.
23. 7. (a) Yao, C-F.; Chen, W.-C.; Lin, Y.-M. Tetrahedron Lett. 1996, 37, 6339.
24. (b) Yao, C.-F.; Kao, K.-S.; Liu, J.-T.; Chu, C-M.; Wang, Y.; Chen, W.-C; Lin, Y.-M.; Yan, M.-C; Liu, J.-Y.; Chuang, M.-C.; Shiue, J.-L. Tetrahedron 1998, 54, 791.
25. 8. Yao, C.-F.; Yang C.-S, Fang, H.-Y. Tetrahedron Lett. 1997, 38, 6419.
26. 9. (a) Hassner, A.; Dehaen, W. Chem. Ber. 1991, 124, 1181.
27. (b) Hassner, A.; Friedman, O.; Dehaen, W. Liebigs A. 1997, 587.
28. (c) Hassner, A.; Murthy, K. S. K. J. Org. Chem. 1989, 54, 5277.
29. 10. Hassner, A.; Dehaen, W. J. Org. Chem. 1990, 55, 5505.
30. 11. Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463.
31. 12. Grundmann C.; Richter, R. J. Org. Chem. 1968, 33, 476.
32. 13. (a) Miyashita, M.; Awen B. Z. E.; Yoshikoshi, A. Synthesis, 1990, 563.
33. (b) Ehrig, V.; Seebach, D. Chem. Ber. 1975, 108, 1961.
34. (c) Seebach, D.; Leitz, H. R.; Ehrig, V. Chem. Ber. 1975, 108, 1924.
35. 14. (a) Bouveault, L; Wahl, A. C. R. Acad. Sci. 1902, 135, 41.
36. (b) Bordwell, F. G.; Garbisch, E. W. J. Org. Chem. 1962, 27, 2322, 3049.
37. 15. Confalone, P. N.; Pizzolato, G.; Confalone, D. L.; Uskokovic, M. R. J. Am. Chem. Soc. 1980, 102, 1954.