Dynamic Stereochemistry and Steric Effects in Overcrowded Ethylenes. Conformational Behavior of Dixanthylenes

Journal of the American Chemical Society

Volumn 101, Issue 3, 1979, Pages 665-671

  Agranat, Israel ^a   Tapuhi, Yitzhak ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001161898     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00497a030     Document Type: Article

References (72)

1. Jackman, L.M.; Cotton, F.A., Ed. “Dynamic Nuclear Magnetic Resonance Spectroscopy”, Academic Press : New York, N.Y., 1975.
2. Oki, M. Angew. Chem., Int. Ed. Engl. 1976, 15, 87.
3. Kalinowski, H.O.; Kessler, H. Top. Stereochem. 1973, 7, 295.
4. Sutherland, I.O. Annu. Rep. NMR Spectrosc. 1971, 4, 71.
5. Kessler, H. Tetrahedron 1974, 30, 1861.
6. Sandstrom, J.; Wennerbeck, I. J. Chem. Soc., Chem. Commun. 1971, 1088.
7. Cundall, R.B. Prog. React. Kinet. 1964, 2, 165.
8. Salem, L.; Rowland, C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92.
9. Ammon, H.L.; Wheeler, G.L. J. Am. Chem. Soc. 1975, 97, 2326.
10. Sandstrom, J.; Sjostrand, U. Tetrahedron 1978, 34, 371.
11. Sandstrom, J.; Sjostrand, U.; Wennerbeck, I. J. Am. Chem. Soc. 1977, 99, 4526.
12. Shvo, Y. Tetrahedron Lett. 1968, 5923.
13. Downing, A.P.; Ollis, W.D.; Sutherland, I.O. J. Chem. Soc. B 1969, 111.
14. Llebman, J.F.; Greenberg, A. Chem. Rev. 1976, 76, 311.
15. Olah, G.A.; Surya Prakash, G.K. J. Org. Chem. 1977, 42, 580.
16. Ferlnga, B.; Wynberg, H. J. Am. Chem. Soc. 1977, 99, 602.
17. Kortum, G. Ber. Bunsenges. Phys. Chem. 1974, 78, 391.
18. Bercovlci, T.; Korenstein, R.; Muszkat, K. A.; Fischer, E.; Pure Appt. Chem. 1970, 24, 531.
19. Day, J.H. Chem. Rev. 1963, 63, 65.
20. Bergmann, E.D. Prog. Org. Chem. 1955, 3, 81.
21. Harnic, E.; Schmidt, G.M.J.; J. Chem. Soc. 1954, 3295.
22. Harnic, E.; Herbstein, F.H.; Schmidt, G.M.J.; Hirshfeld, F.L.; J. Chem. Soc. 1954, 3288.
23. Mills, J.F.D.; Nyburg, S.C. J. Chem. Soc. 1963, 308, 927.
24. Korenstein, R.; Muszkat, K.A.; Sharafy-Ozeri, S.; J. Am. Chem. Soc. 1973, 95, 6177.
25. Korenstein, R.; Muszkat, K.A.; Slifkin, M.A.; Fischer, E. J. Chem. Soc., Perkin Trans. 2 1976, 438.
26. Agranat, I.; Tapuhi, Y. J. Am. Chem. Soc. 1976, 98, 615.
27. Agranat, I.; Tapuhi, Y. Nouveau J. Chim. 1977, 1, 361.
28. Agranat, I.; Tapuhi, Y. J. Am. Chem. Soc., 1978, 100, 5604.
29. Bergmann, E.D.; Weiler-Feilchenfeid, H.; Heller, A.; Brltzmann, C.; Hlrschfeld, A. Tetrahedron, Suppl. 7 1966, 349.
30. Bailey, N.A.; Hull, S.E. Chem. Commun. 1971, 960.
31. Bailey, N.A.; Hull, S.E. Acta Crystallogr., Sect. B 1978, 34, 3289.
32. Gault, I.R.; Ollis, W.D.; Sutherland, I.O. Chem. Commun. 1970, 269.
33. Agranat, I.; Rabinovltz, M.; Weitzen-Dagan, A.; Gosnay, I. J. Chem. Soc., Chem. Commun. 1972, 732.
34. Rabinovltz M.; Agranat, I.; Weitzen-Dagan, A. Tetrahedron Lett. 1974, 1241.
35. Forster, H.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1977, 16, 429.
36. Mislow, K.; Raban, M. Top. Stereochem. 1967, 1, 1.
37. Jennings, W.B. Chem. Rev. 1975, 75, 307.
38. Bartle, K.D.; Jones, D.W. Adv. Org. Chem. 1972, 8, 317.
39. Rabinovltz, M.; Agranat, I.; Bergmann, E.D. Tetrahedron Lett. 1965, 1265.
40. Kessler, H. Angew. Chem., Int. Ed. Engl. 1970, 9, 219.
41. Shanan-Atidi, H.; Bar-Eli, K.H. J. Phys. Chem. 1970, 74, 961.
42. Kost, D.; Carlson, E.H.; Raban, M. Chem. Commun. 1971, 656.
43. Kost, D.; Zeichner, A. Tetrahedron Lett. 1974, 4533.
44. Egan, W.; Tang, R.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1971, 93, 6205.
45. Bernard, M.; Canuel, L.; St-Jacques, M. J. Am. Chem. Soc. 1974, 96, 2929.
46. Newman, R.C.; Jonas, V. J. Org. Chem. 1974, 39, 925.
47. Dahlquist, K.I.; Forsen, S.; Aim, T. Acta Chem. Scand. 1970, 24, 651.
48. Eaton, S.S.; Eaton, G.R. J. Am. Chem. Soc. 1975, 97, 3660.
49. Allerhand, A.; Gutowsky, H.S.; Jonas, J.; Meinzer, R.A. J. Am. Chem. Soc. 1966, 88, 3185.
50. Shoup, R.R.; Becker, E.D., McNeel, M.L. J. Phys. Chem. 1972, 76, 71.
51. Anet, F.A.L.; Anet, R. “Determination of Organic Structures by Physical Methods”, Vol. 3; Nachod, F.C.; Zuckerman, J.J., Ed.; Academic Press : New York, N.Y., 1971; Chapter 7, p 344.
52. Lehn, J.M. Fortschr. Chem. Forsch. 1970, 15, 311.
53. Glasstone, S.; Laidler, K.J., Eyring, H. “The Theory of Rate Processes” International Chemical Series, McGraw-Hill : New York, N.Y., 1941.
54. Raban, M.; Kenney, G.W.J., Jr. Tetrahedron Lett. 1969, 1295.
55. Mislow, K. “Introduction to Stereochemistry”, W.A. Benjamin : New York, N.Y., 1965; p 38.
56. Newman, M.S., Ed. “Steric Effects In Organic Chemistry”, Wiley : New York, N.Y., 1956.
57. Kost, D.; Sprecher, M.S. Tetrahedron Lett. 1977, 1089.
58. Kost, D.; Raban, M. J. Org. Chem. 1976, 41, 1748.
59. Bernardi, F.; Csizrriadia, I.G.; Manglni, A.; Schlegel, H.B.; Whangbo, M.-H.; Wolfe, S. J. Am. Chem. Soc. 1975, 97, 2209.
60. Douglas, J.E.; Rabinovltch, B.S.; Looney, F.S. J. Chem. Phys. 1955, 23, 315.
61. Klstiakowsky, G.B.; Smith, W. R., J. Am. Chem. Soc. 1934, 56, 638.
62. Jensen, F.R.; Noyce, D.S.; Sederholm, C. H.; Berlin, A.J.; J. Am. Chem. Soc, 1962, 84, 386.
63. Anet, F.A.L.; Bourn, A.J.R. J. Am. Chem. Soc, 1967, 89, 760.
64. Bovey, F.A.; Anderson, E.W.; Hood, F.P.; Kornegay, R.L. J. Chem. Phys. 1964, 40, 3099.
65. Pickett, H.M.; Strauss, H.L. J. Am. Chem. Soc. 1970, 92, 7281.
66. Harris, R.K.; Spragg, R.A. J, Chem. Soc. B 1968, 684.
67. Taft, R.W., Jr. J. Am. Chem. Soc. 1953, 75, 4534.
68. Dhar, S.N. J. Chem. Soc. 1920, 1053.
69. Gurgenjanz, G.; V. Kostanecki, S. Ber. 1895, 28, 2310.
70. Ullmann, F.; Zlokasoff, M. Ber. 1905, 38, 2111.
71. Huston, R.C.; Hsieh, T.Y. J. Am. Chem. Soc, 1936, 58, 439.
72. Mustafa, A.; Asker, W.; Sobhy, M.E.-D. J. Org. Chem. 1960, 25, 1519.