Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2561-2563

  Caló, Vincenzo ^a   Nacci, Angelo ^a   Monopoli, Antonio ^a   Fanizzi, Antonello ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; DRUG DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; HETEROCYCLIC COMPOUND; PROPANE; PROPYLENE CARBONATE; QUATERNARY AMMONIUM DERIVATIVE; SOLVENT; TETRABUTYLAMMONIUM;

ARTICLE; CATALYSIS; CHEMISTRY; ENVIRONMENTAL PROTECTION; INDUSTRIAL WASTE; METHODOLOGY; SYNTHESIS;

CARBON DIOXIDE; CATALYSIS; CONSERVATION OF NATURAL RESOURCES; EPOXY COMPOUNDS; ETHYLENE OXIDE; HETEROCYCLIC COMPOUNDS; INDUSTRIAL WASTE; PROPANE; QUATERNARY AMMONIUM COMPOUNDS; SOLVENTS;

EID: 0012414644     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026189w     Document Type: Article

References (21)

1. Behr, A. Carbon Dioxide Activation by Metal Complexes; VCH: New York, 1988.
2. Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155-174.
3. Brindöpke, G. German Pat. DE 3529263, 1987.
4. Baba, A.; Nozaki, T.; Matsuda, H. Bull. Chem. Soc. Jpn. 1987, 60, 1552-1554.
5. Kihara, N.; Hara, N.; Endo, T. J. Org. Chem. 1993, 58, 6198-6202.
6. Kruper, W. J.; Dellar, D. V. J. Org. Chem. 1995, 60, 725-727.
7. Magdesieva, T. V.; Milovanov, S. V.; Lokshin, B. V.; Klemenkova, Z. S.; Tomilova, L. G. Russ. Chem. Bull. 1998, 47, 2137-2145.
8. Kim, H. S.; Kim, J. J.; Lee, B. G.; Jung, O. S.; Jang, H. G.; Kang, S. O. Angew. Chem., Int. Ed. 2000, 39, 4096-4098.
9. Yano, T.; Matsui, H.; Koike, T.; Ishiguro, H.; Fujihara, H.; Yoshihara, M.; Maeshima, T. Chem. Commun. 1997, 1129-1130.
10. Yamaguchi, K.; Ebitani, K.; Yoshida, T.; Yoshida, H.; Kaneda, K. J. Am. Chem. Soc. 1999, 121, 4526-4527.
11. Lu, X. B.; Pan, Y. Z.; Ji, D. F.; He, R. Chin. Chem. Lett. 2000, 11, 589.
12. Deng, Y.; Peng, J. New J. Chem., 2001, 25, 639.
13. Yang, H.; Gu, Y.; Deng, Y.; Shi, F. Chem. Commun. 2002, 274.
14. 2 as described above. The carbonate was distilled or extracted with ethyl acetate.
15. As a proof for this mechanism, we isolated, in some cases, a small quantity of bromohydrines.
16. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: New York, 1988.
17. Caló, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973-8976.
18. Caló, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701-4703.
19. Caló, V.; Nacci, A.;. Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071-6077.
20. Caló, V.; Nacci, A. Z. Naturforsch. 2001, 56a, 702-706.
21. Gannon, T. J.; Law, G.; Watson, P. R.; Carmichael, A. J.; Seddon, K. R. Langmuir 1999, 15, 8429-8434.