On the Migration of a HOOC Group in a Wagner-Meerwein Rearrangement in Superacid Solution: Proof by Double Labeling with Carbon-13

Journal of the American Chemical Society

Volumn 104, Issue 9, 1982, Pages 2631-2632

  Berner, Daniel ^a   Cox, D Phillip ^a   Dahn, Hans ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001024492     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00373a048     Document Type: Letter

References (24)

1. For a review see: Acheson, R. M. Acc. Chem. Res. 1971, 4, 177–186.
2. Kagan, J.; Agdeppa, D. A.; Singh, S. P. Helv. Chim. Acta 1972, 55, 2252–2254.
3. House, H. O. J. Am. Chem. Soc. 1954, 76, 1235–1237.
4. Sing, S. P.; Kagan, J. J. Am. Chem. Soc. 1969, 91, 6198–6199.
5. Wemple, J. J. Am. Chem. Soc. 1970, 92, 6694–6695.
6. Butke, G. P.; Jimenez, F.; Michalik, J.; Gorski, R. A.; Rossi, N. F.; Wemple, J. J. Org. Chem. 1978, 43, 954–960.
7. Durst, T.; Tin, K. C. Tetrahedron Lett. 1970, 2369–2372.
8. Tavarès, D. F.; Estep, R. E.; Blezard, M. Tetrahedron Lett. 1970, 2373–2376.
9. Kagan, J.; Agdeppa, D. A.; Singh, S. P.; Mayers, D. A.; Boyajian, C.; Poorker, C.; Firth, B. E. J. Am. Chem. Soc. 1976, 98, 4581–4588.
10. Kagan, J.; Agdeppa, D. A.; Mayers, D. A.; Singh, S. P.; Walters, M. J.; Wintermute, R. D. J. Org. Chem. 1976, 41, 2355–2362.
11. Plieninger, H.; Suehiro, T. Chem. Ber. 1956, 89, 2789–2794.
12. Plieninger, H.; Arnold, L.; Hoffmann, W. Chem. Ber. 1968, 101, 981–983.
13. Marx, J. N.; Argyle, J. C.; Norman, L. R. J. Am. Chem. Soc. 1974, 96, 2121–2129.
14. Blaise, E. E.; Courtot, A. Bull. Soc. Chim. Fr. 1906, 35, 360–373, 589–600.
15. Phan, T. H.; Dahn, H. Helv. Chim. Acta 1976, 59, 335–348.
16. Cann, P. F.; Warren, S. J. Chem. Soc., Chem. Commun. 1970, 1026–1027.
17. Berner, D.; Dahn, H.; Vogel, P. Helv. Chim. Acta 1980, 63, 2538–2553.
18. Rodé-Gowal, H.; Dahn, H. Helv. Chim. Acta 1973, 56, 2070–2079.
19. Rodé-Gowal, H.; Dao, L. H.; Dahn, H. Helv. Chim. Acta 1974, 57, 2209–2215.
20. Armstrong, F. B.; Hedgecock, C. J. R.; Reary, J. B.; Whitehouse, D.; Crout, D. H. G. J. Chem. Soc., Chem. Commun. 1974, 351–352.
21. Olah, G. A.; White, A. M. J. Am. Chem. Soc. 1967, 89, 3591–3594.
22. Olah, G. A.; White, A. M.; O'Brien, D. H. “Carbonium Ions”; Olah, G. A.; Schleyer, P. V. R., Eds.; Wiley: New York, 1973; Vol. IV, pp 1754–1762.
23. Aebi, A.; Gyurech-Vago, E.; Hofstetter, E.; Waser, P. Pharm. Acta Helv. 1963, 38, 407.
24. For example the rearrangement of cinenic acid to geronic acid: Meinwald, J.; Hwang, H. C.; Christman, D.; Wolf, A. P. J. Am. Chem. Soc. 1960, 82, 483–486.