The first conversion of primary alkyl halides to nitroalkanes under aqueous medium

Journal of Organic Chemistry

Volumn 69, Issue 20, 2004, Pages 6907-6908

  Ballini, Roberto ^a   Barboni, Luciano ^a   Giarlo, Guido ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; NITROGEN COMPOUNDS; SILVER COMPOUNDS; WATER;

ALKYL NITRITES; AQUEOUS MEDIUM; NITROALKANES;

HALOGEN COMPOUNDS;

ALKYL GROUP; HALIDE; NITROALKANE;

ALKYLATION; ARTICLE; CHEMICAL REACTION KINETICS; GAS CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 4644257958     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049048b     Document Type: Article

References (39)

1. (a) Müller, E., Ed. Houben-Weyl: Methoden der Organischen Chemie; Thieme: Stuttgart, 1971; Vol. 10/1.
2. (b) Müller, E., Ed. Houben-Weyl: Methoden der Organischen Chemie; Thieme: Stuttgart, 1992; Vol. E16D/1.
3. (c) Feuer, H., Ed. The Chemistry of the Nitro and Nitroso Group; Wiley-Interscience: New York, 1969, Part 1, 1970; Part 2, 1982, Supplement F.
4. See for example: (a) Wade, P. A.; Kondracki, P. A.; Carrol, P. J. J. Am. Chem. Soc. 1991, 113, 8807-8811. (b) Marchand, A. P.; Rajagopal, D.; Bott, S. G. J. Org. Chem. 1994, 59, 5499-5501.
5. See for example: (a) Wade, P. A.; Kondracki, P. A.; Carrol, P. J. J. Am. Chem. Soc. 1991, 113, 8807-8811. (b) Marchand, A. P.; Rajagopal, D.; Bott, S. G. J. Org. Chem. 1994, 59, 5499-5501.
6. (a) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
7. (b) Feuer, H.; Nielson, A. T. Nitro Compounds: Recent Advances in Synthesis and Chemistry; VCH: New York, 1990.
8. (c) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988.
9. (d) Ballini, R. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1997; Vol. 19, pp 117-184.
10. (a) Barret, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751-762.
11. (b) Varma, R. S.; Kabalka, G. W. Heterocycles 1986, 24, 2645-2677.
12. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
13. (d) Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017-1047.
14. Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanisms; VCH: New York, 1990.
15. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1-18.
16. (a) Kornblum, N. Org. React. 1962, 12, 101.
17. (b) Feuer, H.; Leston, G. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. 4, p 368.
18. An alternative method with pre-prepared anion-exchange resins, in benzene, has been also reported: Gelbard, G.; Colonna, S. Synthesis 1977, 113-116.
19. (a) Amato, J. Science 1993, 259, 1538-1541.
20. (b) Ilman, D. L. Chem. Eng. News 1993, 71, 5-6.
21. (c) Ilman, D. L. Chem. Eng. News 1994, 72, 22-27.
22. (a) Grieco, P. A. Organic Synthesis in Water; Blackie Academic and Professional: London, 1998.
23. (b) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley and Sons: New York, 1997.
24. (c) Lubineau, A. Chem. Ind. 1996, 123.
25. (d) Fringuelli, F.; Piermatti, O.; Pizzo, F. In Target in Heterocycles Systems, Chemistry and Properties; Attanasi, O., Spinelli, D., Eds.; Italian Society of Chemistry: Rome, 1997; Vol. 1, p 57.
26. (e) Li, C. J. Chem. Rev. 1993, 93, 2023-2035.
27. (a) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proc. Int. 1990, 22, 707-746.
28. (b) Ballini, R.; Bosica, G. Recent Research Development in Organic Chemistry; Transworld Research Network: Trivandrum, 1997; Vol. 1, pp 11-24.
29. (c) Ballini, R. Synlett 1999, 1009-1018.
30. Bayada, A.; Lawrence, G. A.; Maeder, M.; O'Leary, M. A. Dalton Trans. 1994, 21, 3107-3111.
31. Hauser, F. M.; Baghdanov, V. M. J. Org. Chem. 1988, 53, 2872-2873.
32. Crandall, J. K.; Reix, T. J. Org. Chem. 1992, 57, 6759-6764.
33. Kornblum, N.; Erickson, A. S.; Kelly, W. J.; Henggeler, B. J. Org. Chem. 1982, 47, 4534-4538.
34. Katritzky, A. R.; Kashmiri, M. A.; Wittmann, D. K. Tetrahedron 1984, 40, 1501-1510.
35. Ballini, R.; Bosica, G.; Fiorini, D.; Giarlo, G. Synthesis 2001, 13, 2003-2006. The spectroscopic data are not reported in the litterature.
36. Jones, R. C. F.; Duller, K. A. M.; Vulto, S. I. E. J. Chem. Soc., Perkin Trans. 1 1998, 411-416.
37. (a) Kornblum, N.; Larso, H. O.; Blackwood, R. K.; Mooberry, D. D.; Oliveto, E. P.; Graham, G. E. J. Am. Chem. Soc. 1956, 78, 1497-1499.
38. (b) Kornblum, N. Org. React. 1962, 12, 101-156.
39. (c) Feuer, H. The Chemistry of Nitro and Nitroso Groups; Interscience Publishers: New York, 1969.