Comparative autoxidation of 3-Carene and α-Pinene: Factors governing regioselective hydrogen abstraction reactions

Tetrahedron

Volumn 54, Issue 3-4, 1998, Pages 593-598

  Rothenberg, Gadi ^a   Yatziv, Yael ^a   Sasson, Yoel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 EPOXYPINANE; 3 CARENE 5 ONE; FREE RADICAL; PINENE; TERPENE; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; CATALYST; CHEMICAL ANALYSIS; ENTROPY; OXYGENATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0032518833     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10319-2     Document Type: Article

References (41)

1. 1. Courtneidge, J. L.; Bush, M., J. Chem. Soc. Per. 1, 1992, 1531-1549.
2. 2. Dimitrov, D.; Sirakova, V.; Stefanova, R., Oxid. Commun., 1984, 7 (3-4), 399-407.
3. 3. Gomes, M. J. T.; Antunes, O. A. C., J. Mol. Catal., 1997, 121, 145-155.
4. 4. Gusevskaya, E.; Gonsalves, J. A., J. Mol. Catal., 1997, 121, 131-137.
5. 5. Alper, H.; Harustiak, M., J. Mol. Catal., 1993, 84, 87-92.
6. 6. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y., J. Org. Chem., 1996, 61,4520-4526.
7. 7. Drago, R. S.; Zuzich, A.; Nyberg, E. D., J. Am. Chem. Soc., 1985, 107, 2898-2903.
8. 8. Morvillo, A.; Bressan, M., J. Mol. Catal., 1986, 37, 63-74.
9. 9. Nam, W.; Kim, H. J.; Kim, S. H.; Ho, R. Y. N.; Valentine, J. S., Inorg. Chem., 1995, 35, 1045-1049.
10. 10. Bystrom, S. E.; Larsson, E. M.; Akermark, B., J. Org. Chem., 1990, 55, 5674-5675.
11. 11. Szmant, H. H., Organic Building Blocks of the Chemical Industry., Wiley: New York, (1989), 386-391.
12. 12. Mukesh, D.; Bhaduri, S.; Khanwalkar, V., Chem. Eng. J., 1988, 38, 153-160.
13. 13. Reddy, M. M.; Punniyamurthy, T.; Iqbal, J., Tetrahedron Lett., 1995, 36(1), 159-162.
14. 14. Sheldon, R. A.; Kochi, J. K. Metal-catalyzed Oxidations of Organic Compounds; Academic: New York, 84, 1981, pp. 25-26.
15. 15. Drago, R. S., Activation of Molecular Oxygen by Transition Metal Complexes. In Dioxygen Activation and Homogeneous Catalytic Oxidation; Simandi, L. I., Ed.; Elsevier: Amsterdam, 1991; pp. 83-91.
16. 16. Bolland, J. L., Trans. Faraday Soc., 1950, 46, 358-367.
17. 17. Beckwith, A. L. J.; Phillipou, G., Aust. J. Chem., 1976, 29, 1277-1294.
18. 18. Bridger, R. F.; Russell, G. A., J. Am. Chem. Soc., 1963, 85, 3754-3765.
19. 19. Howard, J. A.; Ingold, K. U., Can. J. Chem., 1967, 45, 793-802.
20. 20. Walling, C.; Thaler, W., J. Am. Chem. Soc., 1961, 83, 3877-3884.
21. 21. Kooyman, E. C., Disc. Faraday Soc., 1951, 10, 163-174.
22. 22. Ingold, K. U., Intern. Symp. Free Radical Soln., Univ. of Michigan, Ann Arbor, Mich., 1966, 49-67.
23. 23. Russell, G .A.; De Boer, C., J. Am. Chem. Soc., 1963, 85, 3136.
24. 24. Walling, C.; Rieger, A. L.; Tanner, D. D., J. Am. Chem. Soc., 1963, 85, 3129-3134.
25. 25. We have not determined the exact stereochemical configuration of the oxirane ring in 4 and 6, though GCMS analysis indicates two isomers for 4, and only one for 6. Similarly, we cannot say whether 7 is a mixture of two epimers or not.
26. 26. Lajunen, M.; Koskinen, A. M. P., Tetrahedron. Lett., 1994, 35 (25), 4461-4464.
27. 27. Rothenberg, G.; Wiener, H.; Sasson, Y., J. Mol. Catal., submitted for publication, Sept. 1997.
28. 28. Courtneidge, J. L.; Bush, M., J. Chem. Soc. Chem. Commun., 1989, 1227-1229.
29. 29. Villenave, J. -J.; Francois, H.; Lalande, R., Bull. Soc. Chim. Fr., 1970, 599-601.
30. 30. Kolehmainen, E.; Laihia, K.; Heinanen, M.; Rissanen, K.; Frolich, R.; Korvola, J.; Manttari, P.; Kauppinen, R., J. Chem. Soc. Per, 1., 1993, 641-648.
31. 31. Abraham, R. J.; Cooper, M. A.; Whittaker, D., Org. Magn. Reson., 1973, 5 (11), 515-516.
32. 32. Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A., Conformational Analysis; Interscience: New York, 1965, pp. 109-111.
33. 33. Frankel, E. N.; Garwood, R. F.; Vinson, J. R.; Weedon, B. C. L., J. Chem. Soc. Per. 1, 1982, 2707-2713.
34. 34. Cross, B.; Whitham, G. H., J. Chem. Soc., 1961, 1650-1654.
35. 35. Detty, M. R.; Paquette, L. A., J. Org. Chem., 43(6), 1978, 1118-1121. Although this study concerns bishomocycloheptatrienes, where the allylic carbon is part of the cyclopropyl ring, we reason that a similar effect would ease HA from the methylenic positions in 1.
36. 36. Bunce, N. J.; Hadley, M., J. Org. Chem., 1974, 39(15), 2271-2276.
37. 37. King, H. C. A.; Koros, E.; Nelson, S. M., J. Chem . Soc., 1963, 5449-5459.
38. 2) and also in the absence of catalyst (yield ca. 30 % after 25 min).
39. 39. Bohlmann, F.; Zeisberg, R.; Klein, E., Org. Magn. Reson., 1975, 7, 426-432.
40. 40. Giuseppetti, G.; Tadini, C.; Bettinetti, G. P., Acta Cryst., 1992, C 48, 148-150.
41. 41. Baines, D. A.; Cocker, W., J. Chem. Soc. Per. 1, 1975, 2232-2237.