An effort to generalize the thermal isomerization of 6,6-dimethylbicyclo[3.1.1]heptanes and 6,6-dimethylbicyclo[3.1.1]heptenes: Comparative pyrolysis of pinane, α-pinene, and β-pinene

Journal of Analytical and Applied Pyrolysis

Volumn 85, Issue 1-2, 2009, Pages 252-259

  Stolle, A ^a   Ondruschka, B ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Biradicals; Pericyclic reactions; Pyrolysis of renewables; Reaction model

Indexed keywords

HEPTANE; OLEFINS; PYROLYSIS; REACTION INTERMEDIATES;

ACTIVATION PARAMETER; BIRADICALS; FLOW TYPE APPARATUS; PERICYCLIC REACTION; REACTION MODEL; RENEWABLES; THERMAL ISOMERIZATIONS; THERMAL REARRANGEMENT;

MONOTERPENES;

EID: 67349118131     PISSN: 01652370     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jaap.2008.12.002     Document Type: Article

References (52)

1. Eggersdorfer M. In: Eloers B., and Hawkins S. (Eds). Ullmann's Encylopedia of Industrial Chemistry A27 (1996), VCH-Weinheim, Weinheim 267
2. Paiva N.L. J. Plant Growth Regul. 19 (2000) 131
3. Wagner K.H., and Elmadfa I. Ann. Nutr. Metab. 47 (2003) 95
4. Ruzicka L. Helv. Chim. Acta 54 (1971) 1753
5. Banthorpe D.V., Charlwood B.V., and Francis M.J.O. Chem. Rev. 72 (1972) 115
6. Egloff G., Herrman M., Levinson B.L., and Dull M.F. Chem. Rev. 34 (1934) 287
7. Frost A.A., and Pearson R.G. Kinetik und Mechanismus homogener chemischer Reaktionen (1964), Verlag Chemie, Weinheim pp. 349-354
8. Banthorpe D.V., and Whittaker D. Quart. Rev. 29 (1966) 373
9. Naves Y.R. Russ. Chem. Rev. 27 (1968) 779
10. Brown R.F.C. Pyrolytic Methods in Organic Chemistry (1980), Academic Press, New York pp. 250-253
11. Frank G. J. Chem. Soc. B (1968) 130
12. Gajewski J.J., Kuchuk I., Hawkins C.M., and Stine R. Tetrahedron 58 (2002) 6943
13. Coxon J.M., Garland R.P., and Hartshorn M.P. Aust. J. Chem. 25 (1972) 2409
14. Coxon J.M., Garland R.P., and Hartshorn M.P. Aust. J. Chem. 25 (1972) 353
15. Coxon J.M., Garland R.P., and Hartshorn M.P. Aust. J. Chem. 25 (1972) 947
16. Euan Cant P.A., Coxon J.M., and Hartshorn M.P. Aust. J. Chem. 28 (1975) 621
17. Stolle A., Ondruschka B., and Bonrath W. Eur. J. Org. Chem. (2007) 2310
18. Stolle A., Brauns C., Nüchter M., Ondruschka B., Bonrath W., and Findeisen M. Eur. J. Org. Chem. (2006) 3317
19. Brown R.F.C. Pyrolytic Methods in Organic Chemistry (1980), Academic Press, New York p. 41
20. Burwell R.L. J. Am. Chem. Soc. 73 (1951) 4461
21. Riistima K., and Harva O. Finn. Chem. Lett. 4 (1974) 132
22. Stolle A., Bonrath W., Ondruschka B., Kinzel D., and González L. J. Phys. Chem. A 112 (2008) 5885
23. Stolle A., Ondruschka B., and Findeisen M. J. Org. Chem. 73 (2008) 8228
24. Stolle A., Bonrath W., and Ondruschka B. J. Anal. Appl. Pyrol. 83 (2008) 26
25. Weigand E.F., and Schneider H.-J. Org. Magnet. Res. 12 (1979) 637
26. Stolle A., Ondruschka B., Bonrtah W., Netscher T., Findeisen M., and Hoffmann M.M. Chem. Eur. J. 14 (2008) 6805
27. Gowenlock B.G. Quart. Rev. 14 (1960) 133
28. Walsh R. Chem. Soc. Rev. 37 (2008) 686
29. Wellmann R.E., and Walters W.D. J. Am. Chem. Soc. 79 (1952) 1542
30. Chickos J.S., and Frey H.M. J. Chem. Soc., Perk. Trans. II (1987) 365
31. Gajewski J.J. Hydrocarbon Thermal Isomerization. 2nd ed. (2004), Elsevier Academic Press, London pp. 46-50
32. Woodward R.B., and Hoffmann R. Angew. Chem., Int. Ed. Engl. 8 (1969) 781
33. Hoffmann R., and Woodward R.B. Science 167 (1970) 825
34. Srinivasan R., and Kellner S.M.E. J. Am. Chem. Soc. 81 (1959) 5891
35. Rienäcker R. Brennstoff-Chemie 45 (1964) 20
36. Lemée L., Ratier M., Duboudin J.G., and Delmond B. Synth. Commun. 25 (1995) 1313
37. de Pascual Teresa J., Sanchez Bellido I., Alberdi Albistegui M.R., san Feliciano A., and Grande Benito M. Anal. Quim. 74 (1978) 301
38. Sasaki T., Eguchi S., and Yamada H. Tetrahdron Lett. 12 (1971) 99
39. de Pascual Teresa J., Sanchez Bellido I., Alberdi Albistegui M.R., san Feliciano A., and Grande Benito M. Anal. Quim. 74 (1978) 305
40. Kolicheski M.B., Cocco L.C., Mitchell D.A., and Kaminski M. J. Anal. Appl. Pyrol. 80 (2007) 92
41. Tanaka J., Katagiri T., and Izawa K. Bull. Chem. Soc. Jpn. 44 (1970) 130
42. Parker E.D., and Goldblatt L.A. J. Am. Chem. Soc. 72 (1950) 2151
43. Huntsman W.T., and Curry T.H. J. Am. Chem. Soc. 80 (1958) 2252
44. Crowley K.J., and Traynor S.G. Tetrahedron 34 (1978) 2783
45. Huntsman W.D., and Hall R.P. J. Org. Chem. 27 (1962) 1988
46. Strickler H., Ohloff G., and Kovats E.sz. Helv. Chim. Acta 50 (1967) 759
47. Oppolzer W., and Snieckus V. Angew. Chem., Int. Ed. Engl. 17 (1978) 476
48. Egger K.W., and Vitins P. J. Am. Chem. Soc. 96 (1974) 2714
49. Leber P.A., and Baldwin J.E. Acc. Chem. Res. 35 (2002) 279
50. Gajewski J.J. Hydrocarbon Thermal Isomerizations. 2nd ed. (2004), Elsevier Academic Press, London
51. Baldwin J.E., and Leber P.A. Org. Biomol. Chem. 6 (2008) 36
52. Northrop B.H., and Houk K.N. J. Org. Chem. 71 (2006) 3