A new, modulated, oxidative ring cleavage of α-nitrocycloalkanones by Oxone®: Synthesis of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters

Synlett

Volumn , Issue 10, 1998, Pages 1049-1050

  Ballini, Roberto ^a   Curini, Massimo ^b   Epifano, Francesco ^b   Marcotullio, Maria Carla ^b   Rosati, Ornelio ^b  

^a Dipartimento di Scienze Chimiche   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002967732     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5740     Document Type: Article

References (27)

1. Fisher, R. H.; Weitz, H. M. Synthesis 1980, 261.
2. Ballini, R.; Sorrenti, P. Org. Prep. Proc. Int. 1984, 16, 289.
3. Dampawan, P.; Zajac, W. W. Synthesis 1983, 545.
4. Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett. 1993, 34, 1859.
5. Venkat Ram Reddy, M.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 1995, 36, 7149.
6. Stach, H.; Hesse, M. Tetrahedron 1988, 44, 1573.
7. Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proc. Int. 1990, 22, 707.
8. Ballini, R.; Petrini, M. Synthetic Commun. 1986, 16, 1781.
9. Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355.
10. Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1993, 34, 3301.
11. Ballini, R.; Marcantoni, E.; Petrini, M.; Rosini, G. Synthesis 1988, 915.
12. Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531.
13. Ballini, R.; Petrini, M.; Polimanti, O. J. Org. Chem. 1996, 61, 5652.
14. Saika, A. K.; Hazarika, M.; Barua, N. C.; Bezbarua, M. S.; Sharma, R. P.; Ghosh, A. C. Synthesis 1996, 981.
15. Ballini, R.; Barboni, L.; Pintucci, L. Synlett 1997, 1389.
16. Ballini, R.; Bosica, G. Tetrahedron 1997, 55, 16131.
17. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
18. Greenlagh, R. P. Synlett 1992, 235.
19. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. J. Org. Chem. 1995, 60, 8412.
20. Denmark, S. E.; Forbes, D. C.; Hays, D. S.; De Pue, J. S.; Wilde, R. G. J. J. Org. Chem. 1995, 60, 1391.
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. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Synth. Commun. 1998, 28, in press.
24. Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 1998, in press.
25. 4 and evaporated to yield pure dicarboxylic acid 2.
26. 4 and evaporated yielding the pure compound 3.
27. 4: C, 66.09; H, 6.82. Found: C, 66.17; H, 6.90.