Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6754-6759

  Casadei, Maria Antonietta ^a   Moracci, Franco Micheletti ^a   Zappia, Giovanni ^a   Inesi, Achille ^b   Rossi, Leucio ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000778345     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970308h     Document Type: Article

References (48)

1. Adams, P.; Baron; F. A. Chem. Rev. 1965, 65, 567-602.
2. Bergmann, M.; Zervas, K. Ber. Dtsch. Chem. Ges. 1932, 65, 1192-1201.
3. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley and Sons, Inc.: New York, 1991; pp 315-348.
4. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875 and references cited therein.
5. (a) Zielinski, C.; Schäfer, H. J. Tetrahedron Lett. 1994, 35, 5621 -5624.
6. (b) Klotz-Berendes, B.; Schäfer, H. J.; Grehl, M.; Fröhlich, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 189-191.
7. The Pesticide Manual, 10th ed.; Tomlin, C. D. S., Ed.; Crop Protection Publication: Farnham, U.K., 1994.
8. (a) The Pharmacological Basis of Therapeutics, 8th ed.; Goodman, L., Gilman, A., Rall T. W., Nies, A. S., Taylor, P., Eds.; Pergamon Press: New York, 1990.
9. (b) Alexander, J.; Bindra, D. S.; Glass, J. D.; Holahan, M. A.; Renyer, M. L.; Rork, G. S.; Sitko, G. R.; Stranieri, M. T.; Stupienski, R. F.; Veerapanane, H.; Cook, J. J. J. Med. Chem. 1996, 39, 480-486 and references cited therein,
10. (c) Barbachyn, M. R.; Hutchinson, D. K.; Brickner, S. J.; Cynamon, M. H.; Kilburn, J. O.; Klemens, S. P.; Glickman, S. E.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 680-685.
11. (a) Belforte, A.; Belli D'Amico, D.; Calderazzo, F. Chem. Her. 1988, 121, 1891-1897.
12. (b) Romano, V. Chim. Ind. (Milan) 1993, 75, 303-306 and references cited therein,
13. (c) Ragaini, F.; Cenini, S. Chim. Ind. (Milan) 1996, 78, 421-427 and references cited therein.
14. Aresta, M.; Quaranta, M. Proceedings of the International Conference on Carbon Dioxide Utilization, Bari, Italy, 1993; pp 63-77 and references cited therein.
15. (a) Yoshida, U.; Ishii, S.; Watanabe, M.; Yamashita, T. Bull. Chem. Soc. Jpn. 1989, 62, 1534-1538 and references cited therein.
16. (b) Toda, T.; Kitagawa, Y. Angew. Chem., Int. Ed. Engl. 1987, 26, 334-335.
17. Aresta, M.; Quaranta, E. Tetrahedron 1991, 47, 9489-9502.
18. Aresta, M.; Quaranta, E. Tetrahedron 1992, 48, 1515-1530.
19. Casadei, M. A.; Inesi, A.; Micheletti Moracci, F.; Rossi, L. Chem. Commun. 1996, 2575-2576.
20. 2;: Roberts, J. L., Jr; Calderwood, T. S.; Sawyer, D. T. J. Am. Chem. Soc. 1984, 106, 4667-4670.
21. (a) Casadei, M. A.; Cesa, S.; Micheletti Moracci, F.; Inesi, A.; Feroci, M. J. Org. Chem. 1996, 61, 380-383.
22. (b) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Micheletti Moracci, F.; Rossi, L. Tetrahedron 1997, 53, 167-176.
23. Casadei, M. A.; Inesi, A.; Jugelt, A.; Micheletti Moracci, F. J. Chem. Soc., Perkin. Trans, 1 1992, 2001-2004.
24. Katchalski, E.; Ben-Ishai, D. J. Org. Chem., 1950, 15, 1067-1073.
25. Kokotos, G. Synthesis 1990, 299-301.
26. Repke, D. B.; Bates, D. K.; Ferguson, W. J. J. Pharm. Sci, 1978, 67, 1167-1168.
27. Umemura, I.; Miyazaki, N.; Ohigashi, A.; Morinoto, Y. Pept. Chem. 1991, 28, 277-280; Chem. Abstr. 1991, 115, 117, 630z.
28. Umemura, I.; Miyazaki, N.; Ohigashi, A.; Morinoto, Y. Pept. Chem. 1991, 28, 277-280; Chem. Abstr. 1991, 115, 117, 630z.
29. Van den Broek, L. A. G. M.; Fennis, P. J.; Arevalo, M. A.; Lazaro, E.; Ballesta, J. P. G.; Lelieveld, P.; Ottenhejm, C. J. Eur. J. Med. Chem. 1989, 24, 503-510.
30. Elfeldt, P. Ber. Dtsch. Chem. Ges. 1891, 24, 3218-3228.
31. Meine, W. H. J. Am. Chem. Soc. 1956, 78, 3708-3710.
32. Huang, S. B.; Belso, A. S.; Weller, D. D. J. Org. Chem. 1991, 56, 6007-6018.
33. Hardegger, V. E.; Ott, H. Helv. Chim. Acta 1955, 38, 312-320.
34. Curphey, T. J. J. Org. Chem. 1979, 44, 2805-2807.
35. Barluenga, J.; Jimenez, C. N.; Yus, M. J. Chem. Soc. Perkin Trans, 1 1984, 721-725.
36. Cooper, C. S.; Peyton, A. L.; Weinkam, R. J. J. Org. Chem. 1983, 48, 4116-4118.
37. Michman, M.; Patai, S.; Wiesel, Y. J. Chem. Soc. Perkin Trans. 1, 1977, 1705-1710.
38. Torimoto, N.; Shingaki, T..; Nagai, T. Bull. Chem. Soc. Jpn. 1978, 57, 2983-2987.
39. Dicken, C. M.; Lu, F. L.; Nee, M. W.; Bruice, T. C. J. Am. Chem. Soc. 1985, 707, 5776-5789.
40. Tamura, Y.; Haruta, J.; Okuyama, S.; Kita, Y. Tetrahedron Lett. 1978, 79, 3737-3740.
41. Braun, J. V. Ber.Dtsch. Chem. Ges. 1903, 36, 2286-2290.
42. Hall, H. K. J.; Schneider, A. K. J. Am. Chem. Soc. 1958, 80.
43. Foglia, T. A.; Swern, D. J. Org. Chem. 1966, 37, 3625-3631.
44. Ben-Ishai, D. J. Am. Chem. Soc. 1956, 75, 4962-4965.
45. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185-4188.
46. Shibata, J.; Nakamura, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1989, 62, 853-859.
47. Boggs, G. R.; Gerig, J. T. J. Org. Chem. 1969, 34, 1484-1486.
48. Tseng, C. C.; Terashma, S.; Yiamada, S. I. Chem. Pharm. Bull. 1977, 25, 28-40.