Recent progress on the ring cleavage of cyclic 2-nitro ketones by external nucleophiles

Synlett

Volumn , Issue 7, 1999, Pages 1009-1018

  Ballini, Roberto ^a  

^a Dipto Scienze Chimiche dell'Univ   (Italy)

Author keywords

Preparation; Ring cleavage; , Difunctionalized molecules; Nitrocycloalkanones

Indexed keywords

CYCLOALKANONE; CYCLOHEXANONE DERIVATIVE; NITRO DERIVATIVE; ORGANOMETALLIC COMPOUND; REDUCING AGENT;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; PARTIAL DRUG SYNTHESIS; REDUCTION; REVIEW; SYNTHESIS;

EID: 0032797192     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-5732     Document Type: Review

References (46)

1. (a) Fisher, R. H.; Weitz, H. M. Synthesis 1980, 261.
2. (b) Stach, H.; Hesse, M. Tetrahedron 1988, 44, 1573.
3. Sheehan, D.; Vellturo, A. F. African Patent 6,705,789, 1968; C. A. 1969, 70, 57261.
4. Sheehan, D.; Vellturo, A. F. African Patent 6,705,789, 1968; C. A. 1969, 70, 57261.
5. Ozbal, H.; Zajac jr, W. W. J. Org. Chem. 1981, 46, 3082.
6. (a) Dampawan, P.; Zajac jr, W. W. J. Org. Chem. 1982, 47, 1176.
7. (b) Elfehail, F.; Dampawan, P.; Zajac jr, W. W. Synthetic Commun. 1984, 10, 929.
8. Ballini, R.; Sorrenti, P. Org. Prep. Proc. Int. 1984, 16, 289.
9. Fever, H.; Pivawer, P. M. J. Org. Chem. 1966, 31, 3152.
10. Elfehail, F. E.; Zajac jr, W. W. J. Org. Chem. 1981, 46, 5151.
11. Shvarts, I. S.; Yarovenko, V. N.; Krayushkin M. M.; Novikov, S. S.; Sevost'yanova, V. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 1674; C. A. 1976, 85, 176926.
12. Shvarts, I. S.; Yarovenko, V. N.; Krayushkin M. M.; Novikov, S. S.; Sevost'yanova, V. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 1674; C. A. 1976, 85, 176926.
13. Lac Wicz, D. R.; Simmons, T. S.; Kreuz, K. L. US Patent 3,366, 326, 1969, Texaco Inc.; C. A. 1969, 71, 101323.
14. Lac Wicz, D. R.; Simmons, T. S.; Kreuz, K. L. US Patent 3,366, 326, 1969, Texaco Inc.; C. A. 1969, 71, 101323.
15. Andrews, H. British Patent 1,240,836, 1971, Imperial Chemical Ind.; C. A. 1971, 75, 118039.
16. Andrews, H. British Patent 1,240,836, 1971, Imperial Chemical Ind.; C. A. 1971, 75, 118039.
17. Voskuil, W. Dutch Patent 8275, 1970, Stamicarbon N. V.; C. A. 1972, 76, 85458.
18. Voskuil, W. Dutch Patent 8275, 1970, Stamicarbon N. V.; C. A. 1972, 76, 85458.
19. Yamada, S.; Sasak, H.; Tanaka, T. German Auslegeschrift (DAS) 2,210,344, 1974, Toyo Soda Man. Co.; C. A. 1973, 78, 4737.
20. Yamada, S.; Sasak, H.; Tanaka, T. German Auslegeschrift (DAS) 2,210,344, 1974, Toyo Soda Man. Co.; C. A. 1973, 78, 4737.
21. Piwaver, P. M. German Auslegeschrift (DAS) 1964964, 1972, Olin Corp.; C. A. 1970, 73, 98486.
22. Piwaver, P. M. German Auslegeschrift (DAS) 1964964, 1972, Olin Corp.; C. A. 1970, 73, 98486.
23. Baer, H. H.; Naik, S. R. J. Org. Chem. 1970, 35, 2927.
24. Skramstad, J. Tetrahedron Lett. 1970, 11, 955.
25. Scheider, J.; Evans E. L.; Fryer, R. I. J. Org. Chem. 1972, 37, 2604.
26. Dampawan, P. Zajac jr, W. W. Synthesis 1983, 545.
27. Kimura, M.; Kajita, K.; Onoda, N.; Morosawa, S. J. Org. Chem. 1990, 55, 4887.
28. Venkat Ram Reddy, M.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 1995, 36, 7149.
29. Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett. 1993, 34, 1859.
30. Available from Aldrich Chemical Co. or readily prepared according to: Liang, P. Org. Synth. 1955, 3, 803.
31. Rank, V. Tetrahedron Lett. 1991, 32, 5353.
32. Ballini, R.; Petrini, M. Synthetic Commun. 1986, 16, 1781.
33. Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355.
34. Ballini, R.; Papa, F.; Abate, C. Eur. J. Org. Chem. in press.
35. Ballini, R.; Bosica, G.; Gigli, F. Tetrahedron 1998, 54, 7573.
36. Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531.
37. Zürcher, A.; Hesse, M. Helv. Chim. Acta 1987, 70, 1937.
38. Ballini, R.; Marcantoni, E.; Petrini, M.; Rosini, G. Synthesis 1988, 915.
39. Ballini, R.; Bosica, G. Tetrahedron 1997, 53, 16131.
40. Ballini, R.; Curini, M.; Epifanio, F.; Marcotullio, M. C.; Rosati, O. Synlett 1998, 1049.
41. Ballini, R.; Petrini, M.; Polimanti, O. J. Org. Chem. 1996, 61, 5652.
42. Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1993, 34, 3301.
43. Ballini, R.; Bartoli, G.; Gariboldi, P. V.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1993, 58, 3368.
44. Saika, A. K.; Hazarika, M. J.; Barua, N. C.; Bezbarua, M. S.; Sharma, R. P.; Ghosh, A. C. Synthesis 1996, 981.
45. Bezbarua, M.; Saika, A. K.; Barua, N. C.; Kalita, D. Synthesis 1996, 1289.
46. Ballini, R.; Barboni, Pintucci, L. Synlett 1997, 1389.