Effect of deuterium on the kinetics of 1,5-hydrogen shifts: 5-Dideuteriomethylene-2,4,6,7,9-pentamethyl-11,11a-dihydro-12H-naphthacene

Journal of the American Chemical Society

Volumn 129, Issue 9, 2007, Pages 2488-2495

  Von Doering, William E ^a   Keliher, Edmund J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARRHENIUS EQUATION; DEUTERIUM ISOTOPE EFFECT; HYDROGEN ATOMS;

CHEMICAL SHIFT; EXTRAPOLATION; ISOTOPES; REACTION KINETICS; STATISTICAL METHODS;

DEUTERIUM;

5 DIDEUTERIOMETHYLENE 2,4,6,7,9 PENTAMETHYL 11,11A DIHYDRO 12H NAPHTHACENE; DEUTERIUM; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RADIOCHEMISTRY; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 33847656171     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066018c     Document Type: Article

References (36)

1. Roth, W. R.; König, J. Liebigs Ann. Chem. 1966, 699, 24-32.
2. Roth, W. R.; König, J.; Stein, K. Chem. Ber. 1970, 103, 426-439.
3. (a) Liu, Y.-p.; Lynch, G. C.; Truong, T. N.; Lu, D.-h.; Truhlar, D. G.; Garnett, B. C. J. Am. Chem. Soc. 1993, 115, 2408-2415.
4. (b) Chantranupong, L.; Wildman, T. A. J. Am. Chem. Soc. 1990, 112, 4151-4154.
5. (c) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666-2667.
6. (d) Jensen, F.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139-3140.
7. Doering, W. v. E.; Keliher, E. J.; Zhao, X. J. Am. Chem. Soc. 2004, 126, 14206-14216.
8. Doering, W. v. E.; Zhao, X. J. Am. Chem. Soc. 2006, 128, 9080-9085.
9. Muzart, J. Synthesis 1982, 60-61.
10. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392-6394.
11. Doering, W. v. E.; Belfield, K. D.; He, J. J. Am. Chem. Soc. 1993, 115, 5414-5421.
12. Doering, W. v. E.; Benkhoff, J.; Shao, L. J. Am. Chem. Soc. 1999, 121, 962-968.
13. Mulzer, J.; Kühl, U.; Huttner, G.; Evertz, K. Chem. Ber. 1988, 121, 2231-2238.
14. Hayase, S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2004, 126, 10028-10034.
15. In footnote 11 of ref 11, attention is directed to the success of the calculations in the absence of inclusion of a tunneling component.
16. Gupte, S. D.; Nabar, D. P.; Sunthankar, S. V. J. Sci. Ind. Res. 1960, 19B, 411-412.
17. Clar, E.; Kemp, W.; Stewart, D. G. Tetrahedron 1958, 3, 325-333.
18. Roth, W. R.; Fink, R., unpublished.
19. Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 11, 431-441.
20. Sunko, D. E.; Humski, K.; Molojcic, R.; Borcic, S. J. Am. Chem. Soc. 1970, 92, 6534-6538.
21. Barborak, J. C.; Chari, S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1971, 93, 5275-5277.
22. Günther, H.; Pawliczek, J. B.; Ulmen, J.; Grimme, W. Angew. Chem., Int. Ed. Engl. 1972, 11, 517-518.
23. Gajewski, J. J.; Conrad, N. D. J. Am. Chem. Soc. 1979, 101, 6693-6704.
24. Grimme, W.; Grammes, T.; Roth, W. R.; Breuckmann, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 872-874.
25. Grammes, T. Ph.D. Dissertation, "Pericyclic Reactions with Participation of a Double Bond of Benzene," University of Cologne, 1991.
26. Heimgartner, H.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1970, 52, 173-176.
27. Baldwin, J. E.; Reddy, V. P. J. Am. Chem. Soc. 1988, 110, 8223-8228.
28. Roth, W. Tetrahedron Lett. 1964, 1009-1013.
29. a would be lower if two measurements were made each at the highest and lowest temperature rather than four measurements equally spaced in 1/T.
30. D in Table 2, column 6, including the extremes of + and -, and - and + of the estimated uncertainties.
31. Kohen, A., Limbach, H.-H., Eds. Isotope Effects in Chemistry and Biology; CRC Press; 2006.
32. Wayne, W.; Adkins, H. Org. Syn. Col. Vol. III 1955, 367-369.
33. Kim, Y. M.; Kwon, T. W.; Chung, S. K.; Smith, M. B. Synth. Commun. 1999, 29, 343-350.
34. Baldwin, S. W.; O'Neill, T. H. Synth. Commun. 1976, 6, 109-112.
35. Jung, K.-Y.; Koreeda, M. J. Org. Chem. 1989, 54, 5667-5675.
36. Heimgartner, H.; Zsindely, J.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1973, 56, 2924-2945.