Synthesis of mixed acid anhydrides from methane and carbon dioxide in acid solvents

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3193-3196

  Zerella, Mark ^a   Mukhopadhyay, Sudip ^a   Bell, Alexis T ^a  

^a University of California   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACID ANHYDRIDE; CARBON DIOXIDE; METHANE; SOLVENT; SULFURIC ACID; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS;

EID: 0141521621     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0348856     Document Type: Article

References (30)

1. (a) Gesser, H. D.; Hunter, N. R. Catal. Today 1998, 42, 183-189.
2. (b) Lunsford, J. H. Catal. Today 2000, 63, 165-174.
3. (c) Otsuka, K.; Wang, Y. Appl. Catal. A: Gen. 2001, 222, 145-161.
4. (a) Bagno, A.; Bukala, J.; Olah, G. A. J. Org. Chem. 1990, 55, 4284-4289.
5. (b) Lin, M.; Sen, A. Nature 1994, 368, 613-615.
6. (c) Freund, H. J.; Wambach, J.; Seiferth, O.; Dillman, B. German Patent 4428566, 1995.
7. (d) Chaepaikin, G. C.; Bezruchenko, A. P.; Leshcheva, A. A.; Boyko, G. N.; Kuzmenkov, I. V.; Grigoryan, E. H.; Shilov, A. E. J. Mol. Catal. A: Chem. 2001, 169, 89-98.
8. (e) Nishiguchi, T.; Nakata, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1992, 7, 1141-1142.
9. (f) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329-334.
10. (g) Fujiwara, Y.; Kitamura, T.; Taniguchi, Y.; Hayashida, T.; Jinoku, T. Stud. Surf. Sci. Catal. 1998, 119, 349-353.
11. (h) Taniguchi, Y.; Hayashida, T.; Shibasaki, H.; Piao, D.; Kitamura, T.; Yamaji, T.; Fujiwara, Y. Org. Lett. 1999, 1 (4), 557-559
12. (i) Asadullah, M.; Taniguchi, Y.; Kitamura, T.; Fujiwara, Y. Tetrahedron Lett. 1999, 40, 8867-8871.
13. (j) Asadullah, M.; Kitamura, T.; Fujiwara, Y. Angew. Chem., Int. Ed. 2000, 39 (14), 2475-2478.
14. Taniguchi, Y.; Hayashida, T.; Kitamura, T.; Fujiwara, Y. Stud. Surf. Sci. Catal. 1998, 114, 439-442.
15. (a) Wilcox, E. M.; Gogate, M. R.; Spivey, J. J.; Roberts, G. W. Stud. Surf. Sci. Catal. 2001, 136, 259-264.
16. (b) Wilcox, E. M.; Roberts, G. W.; Spivey, J. J. Appl. Catal. A: Gen. 2002, 226, 317-318.
17. 2O was used in a capillary as the lock reference. The corresponding chemical shift for acetic acid was 2.3 to 2.4 ppm, depending on the concentration of acetic acid in the mixture.
18. 19F NMR analysis.
19. -1.
20. Free energy of formation of each species was taken from standard tables except the mixed anhydride for which the value was calculated using group contributions.
21. (a) Basickes, N.; Hogan, T. E.; Sen, A. J. Am. Chem. Soc. 1996, 118, 13111-13112.
22. (b) Lobree, L.; Bell, A. T. Ind. Chem. Res. 2001, 40, 736-742.
23. (c) Mukhopadhyay, S.; Bell, A. T. Ind. Chem. Res. 2002, 41, 5901-5905.
24. (d) Mukhopadhyay, S.; Bell, A. T. Angew. Chem., Int. Ed. 2003, 42, 1019-1023.
25. (e) Mukhopadhyay, S.; Bell, A. T. J. Am. Chem. Soc. 2003, 125, 4406-4407.
26. (f) Mukhopadhyay, S.; Bell, A. T. Org. Process Res. Dev. 2003, 7, 161-163.
27. (g) Mukhopadhyay, S.; Bell, A. T. Angew. Chem., Int. Ed. 2003, 42, 2990-2993.
28. (h) Mukhopadhyay, S.; Bell, A. T. Chem. Commun. 2003, 1590-1591.
29. (i) Mukhopadhyay, S.; Bell, A. T. Org. Process Res. Dev. 2003, in press.
30. 4 in this case.