The conversion of saturated hydrocarbons into carboxylic acids using Fe(CO)5-H2O2 oxidation

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8137-8140

  Barton, Derek H R ^a   Delanghe, Nathalie C ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0030569387     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01892-8     Document Type: Article

References (19)

1. 1 Barton, D. H. R. ; Doller, D. Acc. Chem. Res. 1992, 25, 504-512.
2. 2 Barton, D. H. R. ; Hu, B. ; Taylor, D. K. ; Rojas-Wahl, R. V. Tetrahedron Lett. 1996, 37, 1133-1136.
3. 3 Bardin, C.; Barton, D. H. R. ; Hu, B. ; Rojas-Wahl, R. U. ; Taylor, D. K. Ibid. 1994, 35, 5805-5808. Barton, D. H. R. ; Chabot, B. ; Delanghe, N. C. ; Hu, B. ; Le Gloahec, V. N. ; Rojas-Wahl, R. U. Tetrahedron Lett. 1995,36, 7007-7010. Barton, D. H. R. ; Hu, B. ; Taylor, D. K. ; Rojas-Wahl, R. V. J. Chem. Soc. (Perkin Trans.2), 1996, in press.
4. 3 Bardin, C.; Barton, D. H. R. ; Hu, B. ; Rojas-Wahl, R. U. ; Taylor, D. K. Ibid. 1994, 35, 5805-5808. Barton, D. H. R. ; Chabot, B. ; Delanghe, N. C. ; Hu, B. ; Le Gloahec, V. N. ; Rojas-Wahl, R. U. Tetrahedron Lett. 1995,36, 7007-7010. Barton, D. H. R. ; Hu, B. ; Taylor, D. K. ; Rojas-Wahl, R. V. J. Chem. Soc. (Perkin Trans.2), 1996, in press.
5. 3 Bardin, C.; Barton, D. H. R. ; Hu, B. ; Rojas-Wahl, R. U. ; Taylor, D. K. Ibid. 1994, 35, 5805-5808. Barton, D. H. R. ; Chabot, B. ; Delanghe, N. C. ; Hu, B. ; Le Gloahec, V. N. ; Rojas-Wahl, R. U. Tetrahedron Lett. 1995,36, 7007-7010. Barton, D. H. R. ; Hu, B. ; Taylor, D. K. ; Rojas-Wahl, R. V. J. Chem. Soc. (Perkin Trans.2), 1996, in press.
6. 4 Barton, D. H. R. ; Bévière, S. D. ; Chavasiri, W. ; Doller, D. ; Liu, W.-G. ; Reibenpies, J. H. New J. Chem. 1992, 16, 1019-1029. Sawyer, D. T. ; Kang, C. ; Llobet, A. ; Redman, C. J. Am. Chem. Soc. 1993, 115, 5817-5818. Hage, J. P. ; Llobet, A. ; Sawyer, D. T. Bioorg. Med. Chem. Lett. 1995, 3, 1383-1388.
7. 4 Barton, D. H. R. ; Bévière, S. D. ; Chavasiri, W. ; Doller, D. ; Liu, W.-G. ; Reibenpies, J. H. New J. Chem. 1992, 16, 1019-1029. Sawyer, D. T. ; Kang, C. ; Llobet, A. ; Redman, C. J. Am. Chem. Soc. 1993, 115, 5817-5818. Hage, J. P. ; Llobet, A. ; Sawyer, D. T. Bioorg. Med. Chem. Lett. 1995, 3, 1383-1388.
8. 4 Barton, D. H. R. ; Bévière, S. D. ; Chavasiri, W. ; Doller, D. ; Liu, W.-G. ; Reibenpies, J. H. New J. Chem. 1992, 16, 1019-1029. Sawyer, D. T. ; Kang, C. ; Llobet, A. ; Redman, C. J. Am. Chem. Soc. 1993, 115, 5817-5818. Hage, J. P. ; Llobet, A. ; Sawyer, D. T. Bioorg. Med. Chem. Lett. 1995, 3, 1383-1388.
9. 5 Barton, D. H. R. ; Beck, A. H. ; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555-1558.
10. 6 Clark, L. J. Analytical Chemistry 1962, 34, 348-352.
11. 2 (10 mmol)) it gave 0.38 mmol of iron pentacarbonyl remaining.
12. 8 Alaise, V. A. ; Hall, R. T. ; Staats, F. C. and Becker, W. W. Analytical Chemistry 1947, 19, 347-351.
13. 9 Morvillo, A. ; Forti, L. ; Bressan, M. New J. Chem. 1995, 19, 951-957.
14. 10 Semenoff, N. Chemical Kinetics and Chain Reactions; Fowler R. H. , Kapitza, P., Eds; Clarendon Press: Oxford; 1935, Chap.V, 127-139.
15. 2. The gases formed were bubbled, at a low flow rate, trough these traps for 3.5 h. The precipitate obtained was filtered and dried in an oven before weighing.
16. 12 Barton, D. H. R. in collaboration with Parekh, S. I. Half a Century of Free Radical Chemistry; Radicati di Brozolo, L.A., Scaola Normale Superiore Pisa, Eds; Cambridge University Press: 1993.
17. 13 Field, L. D. ; Baker, M. V. J. Am. Chem. Soc. 1986, 108, 7433-7434; Field, L. D. ; Baker, M. V. J. Am. Chem. Soc. 1987, 109, 2825-2826; Whittlesey, M. K. ; Mawby, R. J. ; Osman, R. ; Perutz, R. N. ; Field, L. D. ; Wilkinson, M. P. ; George, M. W. J. Am. Chem. Soc. 1993, 115, 8627-8637.
18. 13 Field, L. D. ; Baker, M. V. J. Am. Chem. Soc. 1986, 108, 7433-7434; Field, L. D. ; Baker, M. V. J. Am. Chem. Soc. 1987, 109, 2825-2826; Whittlesey, M. K. ; Mawby, R. J. ; Osman, R. ; Perutz, R. N. ; Field, L. D. ; Wilkinson, M. P. ; George, M. W. J. Am. Chem. Soc. 1993, 115, 8627-8637.
19. 13 Field, L. D. ; Baker, M. V. J. Am. Chem. Soc. 1986, 108, 7433-7434; Field, L. D. ; Baker, M. V. J. Am. Chem. Soc. 1987, 109, 2825-2826; Whittlesey, M. K. ; Mawby, R. J. ; Osman, R. ; Perutz, R. N. ; Field, L. D. ; Wilkinson, M. P. ; George, M. W. J. Am. Chem. Soc. 1993, 115, 8627-8637.