Heavy-Atom Tunneling as the Dominant Pathway in a Solution-Phase Reaction? Bond Shift in Antiaromatic Annulenes

Journal of the American Chemical Society

Volumn 105, Issue 6, 1983, Pages 1700-1701

  Carpenter, Barry K ^a  

^a Department of Obstetrics Gynecology   (United States)

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Indexed keywords

EID: 33845549947     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00344a073     Document Type: Article

References (18)

1. There are, of course, some exceptions. See, for example: Kaldor, S.B.; Saunders, W.H. J. Am. Chem. Soc. 1979, 101, 7594-7599.
2. Buchwalter, S.L.; Gloss, G.L. J. Am. Chem. Soc. 1975, 97, 3857-3858.
3. Especially relevant to the present problem: Fong, F.K. J. Am. Chem. Soc. 1974, 96, 7638-7646.
4. Dewar, M.J.S.; Komornicki, A. J. Am. Chem. Soc. 1977, 99, 6174-6179.
5. Newton, M.D.; Jafri, J.A. J. Am. Chem. Soc. 1978, 100, 5012-5017.
6. Borden, W.T.; Davidson, E.R.; Hart, P. J. Am. Chem. Soc. 1978, 100, 388-392.
7. -1 for this mode: Schaad, L.J.; Hess, B.A.; Ewig, C.S.J. Org. Chem. 1982, 47, 2904-2906.
8. Kollmar, H.; Staemmler, V. J. Am. Chem. Soc. 1977, 99, 3583-3587.
9. Bell, R.P. Trans. Faraday Soc. 1959, 55, 1-3.
10. Schutte, C.J.H. “The Wave Mechanics of Atoms, Molecules and Ions”; Arnold: London, 1968; p. 50.
11. Actually there should be some splitting of the energy levels due to interaction between the wave functions for the two oscillators (see ref 9, pp. 69 ff) but this has been neglected for the present purposes.
12. Bell, R.P. “The Proton in Chemistry”, 2nd ed.; Cornell University Press; Ithaca, NY, 1973; p. 274.
13. Whitman, D.W.; Carpenter, B.K. J. Am. Chem. Soc. 1982, 104, 6473-6474. This experiment was actually conducted on cyclobutadiene-i/2, but the extra mass makes a negligible contribution to the overall effect.
14. For an example and some leading references See: Brunton, G.; Griller, D.; Barclay, L.R.C.; Ingold, K.U. J. Am. Chem. Soc. 1976, 98, 6803-6811.
15. Naor, R.; Luz, Z. J. Chem. Phys. 1982, 76, 5662-5664.
16. Borden, W.T.; Davidson, E.R. J. Am. Chem. Soc. 1980, 102, 7958-7960.
17. Maier, G.; Kalinowski, H.-O.; Euler, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 693-694.
18. Paquette, L.A. Pure Appl. Chem. 1982, 54, 987-1004.