Acid-Catalyzed Rearrangements of Cyclobutanones

Journal of the American Chemical Society

Volumn 93, Issue 3, 1971, Pages 657-665

  Erman, William F ^a,b   Treptow, Richard S ^a,b   Bakuzis, Peter ^a,b   Wenkert, Ernest ^a,b  

^a PROCTER AND GAMBLE COMPANY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001668680     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00732a018     Document Type: Article

References (47)

1. W. F. Erman, J. Amer. Chem. Soc., 91, 779 (1969).
2. W. F. Erman, Abstracts, 5th International Symposium on Natural Products, London, England, July 8–13, 1968, p 383.
3. R. Breslow in “Molecular Rearrangements,” P. de Mayo, Ed., Interscience, New York, N. Y., 1963, Chapter 4, pp 259–276.
4. M. S. Silver, M. C. Caserio, H. E. Rice, and J. D. Roberts, J. Amer. Chem. Soc., 83, 3671 (1961).
5. T. J. Katz and R. Dessau, J. Amer. Chem. Soc., 85, 2172 (1963).
6. W. F. Erman, J. Amer. Chem. Soc., 89, 3828 (1967).
7. J. J. Hurst and G. H. Whitham, J. Chem. Soc., 2864 (1960).
8. J. J. Beereboom, J. Amer. Chem. Soc., 85, 3525 (1963).
9. J. Org. Chem., 30, 4230 (1965).
10. G. O. Schenck, O. A. NeumUUer, G. Ohloff, and S. Schroeter, Justus Liebigs Ann. Chem., 687, 26 (1965).
11. Ch. Balant, Ch. A. Vodoz, H. Kappeler, and H. Schinz, Helv. Chim. Acta, 34, 722 (1951).
12. M. Kotake and H. Nonaka, Justus Liebigs Ann. Chem., 607, 153 (1957).
13. L. J. Bellamy, “The Infrared Spectra of Complex Molecules,” 2nd ed, Wiley, New York, N. Y., 1958, p 132.
14. L. J. Bellamy, “The Infrared Spectra of Complex Molecules,” 2nd ed, Wiley, New York, N. Y., 1958, p 13.
15. L. J. Bellamy, “The Infrared Spectra of Complex Molecules,” 2nd ed, Wiley, New York, N. Y., 1958, p 34.
16. U. A. Huber, Ph.D. Dissertation, University of Zürich, 1970, pp 37, 85.
17. E. Wenkert, P. Bakuzis, R. J. Baumgarten, C. L. Leicht, and H. P. Schenk, J. Amer. Chem. Soc., in press.
18. K. B. Wiberg and G. W. Klein, Tetrahedron Lett., 1043 (1963).
19. S. Julia and C. Gueremy, Bull. Soc. Chim. Fr., 2994 (1965).
20. F. Nerdel, D. Frank, and H. Marschall, Chem. Ber., 100, 720 (1967).
21. V. Georgian, L. Georgian, A. V. Robertson, and L. F. Johnson, Tetrahedron, 19, 1219 (1963).
22. K. Griesbaum, W. Nacgele, and G. G. Wanless, J. Amer. Chem. Soc., 87, 3151 (1965).
23. R. M. Dodson, J. R. Lewis, W. P. Webb, E. Wenkert, and R. D. Youssefyeh, J. Amer. Chem. Soc., 83, 938(1961).
24. E. Wenkert, P. Bakuzis, R. J. Baumgarten, D. Doddrell, P. W. Jeffs, C. L. Leicht, R. A. Mueller, and A. Yoshikoshi, J. Amer. Chem. Soc., 92, 1617 (1970).
25. E. Wenkert, B. L. Mylari, and L. L. Davis, J. Amer. Chem. Soc., 90, 3870 (1968).
26. W. Briigel, Compiler, “Nuclear Magnetic Resonance Spectra and Chemical Structure,” Vol. I, Academic Press, New York, N. Y., 1967, p 55 and ref 5.
27. A. Moscowitz, K. Mislow, M. A. W. Glass, and C. Djerassi, J. Amer. Chem. Soc., 84, 1945 (1962).
28. R. C. Cookson and S. MacKenzie, Proc. Chem. Soc., 423 (1961).
29. R. C. Cookson and J. Hudec, J. Chem. Soc., 429 (1962).
30. S. F. Mason, J. Amer. Chem. Soc., 3285 (1962).
31. R. E. Ballard, S. F. Mason, and G. W. Vane, Trans. Faraday Soc., 59, 775 (1963).
32. R. B. Bates, M. J. Onore, S. K. Pak-nikar, and C. Steelink, Chem. Commun., 1037 (1967).
33. E. P. Blanchard, Jr., Chem. Ind. (London), 293 (1958).
34. W. Reusch, D. F. Anderson, and C. K. Johnson, J. Amer. Chem. Soc., 90, 4988 (1968).
35. H. Labhart and G. Wagniere, Helv. Chim. Acta, 42, 2219 (1959).
36. A. Moscowitz, A. E. Hansen, L. S. Forster, and K. Rosenheck, Biopolym., Symp., No. 1, 75 (1964).
37. J. D. Roberts and C. M. Sharts, Org. React., 12, 1 (1962).
38. R. H. Hasek and J. C. Martin, J. Org. Chem., 28, 1468 (1963).
39. W. T. Brady and H. R. O'Neal, J. Org. Chem., 32, 612, 2704 (1967).
40. R. Huisgen, L. A. Feiler, and P. Otto, Tetrahedron Lett., 4485 (1968).
41. R. Huisgen and P. Otto, Tetrahedron Lett., 4491 (1968).
42. G. Binsch, L. A. Feiler, and R. Huisgen, Tetrahedron Lett., 4497 (1968).
43. R. B. Woodward and R. Hoffmann, Angew. Chem., Int. Ed. Engl., 8, 847 (1969).
44. M. Rey, S. Roberts, A. Dieffenbacher, and A. S. Dreiding, Helv. Chim. Acta, 53, 417 (1970).
45. P. R. Brook, J. M. Harrison, and A. J. Duke, Chem. Commun., 589 (1970).
46. H. W. Thielmann and E. Hecker, Justus Liebigs Ann. Chem., 728, 158 (1969).
47. R. N. McDonald and C. E. Reineke, J. Org. Chem., 32, 1888 (1967).