Gas-Phase Acidities and Heats of Formation of 2,4- and 2,5-Cyclohexadien-1-one, the Keto Tautomers of Phenol

Journal of the American Chemical Society

Volumn 108, Issue 19, 1986, Pages 5699-5701

  Shiner, Christopher S ^a   Vorndam, Paul E ^a   Kass, Steven R ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845373648     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00279a006     Document Type: Article

References (36)

1. Lasne, M.-C.; Ripoll, J.-L. Tetrahedron Lett. 1980, 21, 463–464.
2. DePuy, C. H.; Grabowski, J. J.; Bierbaum, V. M. Science (Washington, DC) 1982, 218, 955–960.
3. DePuy, C. H.; Bierbaum, V. M. Acc. Chem. Res. 1981, 14, 146–153, and references cited therein.
4. Bartmess, J. E.; McIver, R. T., Jr. In Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Vol. 2, Chapter 11.
5. van Velzen, P. N. T.; van der Hart, W. J.; van der Greef, J.; Nibbering, N. M. M.; Gross, M. L. J. Am. Chem. Soc. 1982, 104, 1208–1212.
6. Biali, S. E.; Depke, G.; Rappoport, Z.; Schwarz, H. J. Am. Chem. Soc. 1984, 106, 496–501.
7. Lasne, M.-C.; Ripoll, J.-L. Synthesis 1985, 121–143.
8. Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974–4976.
9. Toullec, J. Adv. Phys. Org. Chem. 1982, 18, 1–77.
10. Nugiel, D. A.; Rappo-port, Z. J. Am. Chem. Soc. 1985, 107, 3669–3676.
11. Lidert, Z.; McCague, R.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1985, 383–389.
12. Hart, H. Chem. Rev. 1979, 79, 515–528.
13. Capon, B.; Siddhanta, A. K.; Zucco, C. J. Org. Chem. 1985, 50, 3580–3584.
14. Chiang, Y.; Kresge, A. J.; Tang, Y. S.; Wirz, J. J. Am. Chem. Soc. 1984, 106, 460–462.
15. Capon, B.; Zucco, C. J. Am. Chem. Soc. 1982, 104, 7567–7572.
16. Capon, B.; Siddhanta, A. K. Tetrahedron Lett. 1982, 23, 3199–3203.
17. Ripoll, J.-L. Nouv. J. Chim. 1979, 3, 195–198.
18. Baigrie, L. M.; Cox, R. A.; Slebocka-Tilk, H.; Tencer, M.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 3640–3645.
19. Holmes, J. L.; Lossing, F. P. J. Am. Chem. Soc. 1982, 104, 2648–2649.
20. Turecek, F. J. Chem. Soc., Chem. Commun. 1984, 1374–1375.
21. Schaffner, K.; Demuth, M. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 281–348.
22. Turro, N. J. Modern Molecular Photochemistry; Benjamin/Cummings: Menlo Park, CA, 1978; pp 512–516.
23. Schuster, D. I. Acc. Chem. Res, 1978, 11, 65–73.
24. Miller, B. Acc. Chem. Res 1975, 8, 245–256.
25. Perkins, M. J.; Ward, P. Mech. Mol. Migr. 1971, 4, 55–112.
26. Birch, A. J.; Chamberlain, K. B. Org. Synth. 1977, 57, 107–112.
27. DePuy, C. H.; Jones, T.; Parton, R. L. J. Am. Chem. Soc. 1974, 96, 5602–5604.
28. Takamuku, S.; Matsumoto, H.; Hori, A.; Sakurai, H. J. Am. Chem. Soc. 1980, 102, 1441–1443.
29. Jenneskens, L. W.; de Wolf, W. H.; Bickelhaupt, F. Tetrahedron 1985, 41, 3779–3784.
30. Tee, O. S.; Iyengar, N. R. J. Am. Chem. Soc. 1985, 107, 455–459.
31. Tee, O. S.; Iyengar, N. R. J. Chem. 1984, 62, 2803–2812.
32. Cox, J. D.; Pilcher, G. Thermochemistry of Organic & Organometallic Compounds;, Academic Press: New York, 1970; pp 208–209.
33. Banks, A.; Mains, G. J.; Bock, C. W.; Trachtman, M.; George, P. J. Mol. Struct. 1979, 56, 267–275.
34. Bartmess, J. E. J. Am. Chem. Soc. 1982, 104, 335–337.
35. Wiberg, K. B.; Wasserman, D. J.; Martin, E. J.; Murcko, M. A. J. Am. Chem. Soc. 1985, 107, 6019–6022.
36. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.