Oxidative ring cleavage of 2-nitrocycloalkanones: Synthesis and radical-induced transformations of methyl ω,ω-dihalo-ω-nitroalkanoates

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5652-5655

  Ballini, Roberto ^a   Petrini, Marino ^a   Polimanti, Olga ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002087089     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960488f     Document Type: Article

References (24)

1. Reviews: (a) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proc. Int. 1990, 22, 707. (b) Fischer, R. H.; Weitz, H. M. Synthesis 1980, 261.
2. Reviews: (a) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proc. Int. 1990, 22, 707. (b) Fischer, R. H.; Weitz, H. M. Synthesis 1980, 261.
3. For some recent examples see: (a) Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1993, 34, 3301. (b) Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355. (c) Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531.
4. For some recent examples see: (a) Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1993, 34, 3301. (b) Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355. (c) Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531.
5. For some recent examples see: (a) Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1993, 34, 3301. (b) Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355. (c) Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531.
6. (a) Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett. 1993, 34, 1859. For a complete mechanistic study of this procedure see: Rathore, R.; Kochi, J. K. J. Org. Chem. 1996, 61, 627.
7. (a) Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett. 1993, 34, 1859. For a complete mechanistic study of this procedure see: Rathore, R.; Kochi, J. K. J. Org. Chem. 1996, 61, 627.
8. (b) Venkat Ram Reddy, M.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 1995, 36, 7149.
9. (c) Dampawan, P.; Zajac, W. W. Synthesis 1983, 545.
10. (d) Ballini, R.; Sorrenti, P. Org. Prep. Proc. Int. 1984, 16, 289.
11. Ballini, R.; Marcantoni, E.; Petrini, M.; Rosini, G. Synthesis 1988, 915.
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17. Similar results can be obtained with 2-(phenylsulfonyl)cycloalkanones but monochlorinated phenylsulfonyl derivatives are obtained in this instance since the open chain α-chlorophenyl sulfone is less prone to chlorination: Sholtz, D. Liebigs Ann. Chem. 1984, 264.
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20. Dichlorides are usually reduced using the tributyltin hydride-triethylborane couple: (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem Soc. Jpn. 1989, 63, 143. (b) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515.
21. Dichlorides are usually reduced using the tributyltin hydride-triethylborane couple: (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem Soc. Jpn. 1989, 63, 143. (b) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515.
22. Curran, D. P. Synthesis 1988, 489.
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24. Ono, N.; Zinsmeister, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1985, 58, 1069.