A new method for the one-step conversion of oximes into gem-halo-nitro derivatives

Tetrahedron

Volumn 55, Issue 19, 1999, Pages 6211-6218

  Curini, Massimo ^a   Epifano, Francesco ^a   Marcotullio, Maria Carla ^a   Rosati, Ornelio ^a   Rossi, Monia ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Halogenation; Nitro compounds; Oxidation; Oximes

Indexed keywords

HALIDE; NITRO DERIVATIVE; OXIME; POTASSIUM BROMIDE; POTASSIUM HYDROGEN MONOPERSULFATE; SODIUM CHLORIDE; SULFATE; UNCLASSIFIED DRUG;

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

EID: 0033532168     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00265-3     Document Type: Article

References (29)

1. Marchand, A.P.; Suri S.C. J. Org. Chem. 1984, 49, 2041.
2. Marchand, A.P.; Arney, B.E. Jr.; Dave, P.R. J. Org. Chem. 1988, 53, 443.
3. Baum, K.; Archibald, T.G. J. Org. Chem. 1988, 53, 4645.
4. Marchand, A.P.; Reddy, D.S. J. Org. Chem. 1984, 49, 4078.
5. Wade, P.A.; Dailey, W.P.; Carroll, P.J. J. Am. Chem. Soc. 1987, 109, 5452.
6. Paquette, L.A.; Waykole, L.M.; Shen, C. J. Org. Chem. 1988, 53, 4969.
7. Archibald, T.G.; Garver, L.G.; Baum, K.; Cohen, M.C. J. Org. Chem. 1989, 54, 2869.
8. Corey, E.J.; Estreicher, H. Tetrahedron Lett. 1980, 21, 1117.
9. Iffland, D.C.; Criner, G.X. J. Am. Chem. Soc. 1953, 75, 4047.
10. Iffland, D.C.; Criner, G.X.; Koral, M.; Lotspeich, F.J.; Papanastassiou, Z.B.; White, S.M. Jr. J. Am. Chem. Soc. 1953, 75, 4044.
11. Ibne-Rasa, K.M.; Edwards, J.O.; Kost, M.P.; Gallopo, A.R. Chem. Ind. (London) 1974, 23, 964.
12. Barnes, M.W.; Patterson, J.M. J. Org. Chem. 1976, 41, 733.
13. Walters, R.T.; Zajac, W.W.; Woods, J.M. J. Org. Chem. 1991, 56, 316.
14. Zaks, A.; Yabannavar, A.Y.; Dodds, D.R.; Evans, A.C.; Pradip, R.D.; Malchow, R.J. J. Org. Chem. 1996, 61, 8692
15. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. Tetrahedron Lett. 1998, 39, 4385.
16. Greenhalgh, R.P. Synlett 1992, 235.
17. Murray, R.W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
18. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. J. Org. Chem. 1995, 60, 8412.
19. Denmark, S.E.; Forbes, D.C.; Hays, D.S.; DePue, J.S.; Wilde, R.G. J. Org. Chem. 1995, 60, 1391.
20. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. Synth. Comm. 1998, 28, 3057.
21. Hirano, M.; Oose, M.; Morimoto, T. Chem. Lett. 1991, 331.
22. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. Synlett 1996, 767.
23. Ballini, R.; Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. Synlett 1998, 1149.
24. Dieter, R.K.; Nice, L.E.; Velu, S.E. Tetrahedron Lett. 1996, 37, 2377.
25. Kresze, G.; Mayer, N.M.; Winkler, J. Liebigs Ann. Chem. 1971, 747, 171.
26. A discussion of the stereochemical lability of gem-chloro-nitroso compounds may be found in refs. 9, 21 and in the following: Kresze, G; Bosch, T.; Winkler, J. Liebigs Ann. Chem. 1975, 1009; Hope, A.J.; Mitchell, S. J. Chem. Soc. 1954, 4215; Hope, A.J.; Mitchell, S.J. ibid. 1953, 3483.
27. A discussion of the stereochemical lability of gem-chloro-nitroso compounds may be found in refs. 9, 21 and in the following: Kresze, G; Bosch, T.; Winkler, J. Liebigs Ann. Chem. 1975, 1009; Hope, A.J.; Mitchell, S. J. Chem. Soc. 1954, 4215; Hope, A.J.; Mitchell, S.J. ibid. 1953, 3483.
28. A discussion of the stereochemical lability of gem-chloro-nitroso compounds may be found in refs. 9, 21 and in the following: Kresze, G; Bosch, T.; Winkler, J. Liebigs Ann. Chem. 1975, 1009; Hope, A.J.; Mitchell, S. J. Chem. Soc. 1954, 4215; Hope, A.J.; Mitchell, S.J. ibid. 1953, 3483.
29. Sandler, S.R.; Karo, W. Organic Functional Groups Preparations. New York: Academic Press, 1972. 3, 372.