Analysis of Isomerization in Compounds Displaying Restricted Rotation of Aryl Groups

Journal of the American Chemical Society

Volumn 95, Issue 5, 1973, Pages 1535-1547

  Gust, Devens ^a   Mislow, Kurt ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947087968     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00786a031     Document Type: Article

References (102)

1. I. O. Sutherland, Annu. Rep. NMR (Nucl. Magn. Resonance) Spectrosc., 4, 71 (1971).
2. S. Wolfe, A. Rauk, L. M. Tel, and I. G. Csizmadia, J. Chem. Soc. B, 136 (1971).
3. M. J. Sabacky, S. M. Johnson, J. C. Martin, and I. C. Paul, J. Amer. Chem. Soc., 91, 7542 (1969).
4. J. Trotter, Can. J. Chem., 41, 14 (1963).
5. J. Trotter, Acta Crystallogr., 16, 1187 (1963).
6. J. J. Daly, J. Chem. Soc., 3799 (1964).
7. R. A. Shaw, M. Woods, T. S. Cameron, and B. Dahlén, Chem. Ind. (London), 151 (1971).
8. H.-J. Kuhn and K. Plieth, Naturwissenschaften, 53, 359 (1966).
9. D. M. Hawley and G. Ferguson, J. Chem. Soc. A, 2059 (1968).
10. A. Rieker and H. Kessler, Tetrahedron Lett., 1227 (1969).
11. H. Kessler, A. Moosmayer, and A. Rieker, Tetrahedron, 25, 287 (1969).
12. P. Andersen, Acta Chem. Scand., 19, 622 (1965).
13. R. S. Cahn, C. Ingold, and V. Prelog, Angew. Chem., Int. Ed. Engl., 5, 385 (1966).
14. J. W. Rakshys, Jr., S. V. McKinley, and H. H. Freedman, J. Amer. Chem. Soc., 92, 3518 (1970).
15. J. W. Rakshys, Jr., S. V. McKinley, and H. H. Freedman, J. Amer. Chem. Soc., 93, 6522 (1971).
16. F. Strohbusch, Tetrahedron, 28, 1915 (1972).
17. R. J. Kurland, I. I. Schuster, and A. K. Colter, J. Amer. Chem. Soc., 87, 2279 (1965).
18. F. Harary, “Graph Theory,” Addison-Wesley, Reading, Mass., 1969, p 10.
19. K. Mislow, “Introduction to Stereochemistry,” W. A. Benjamin, New York, N. Y., 1965, p 93.
20. G. N. Lewis and M. Calvin, Chem. Rev., 25, 273 (1939).
21. G. N. Lewis, T. T. Magel, and D. Lipkin, J. Amer. Chem. Soc., 64, 1774 (1942).
22. F. Seel, Naturwissenschaften, 31, 504 (1943).
23. N. C. Deno, J. J. Jaruzelski, and A. Schriesheim, J. Org. Chem., 19, 155 (1954).
24. N. C. Deno, P. T. Groves, and G. Saines, J. Amer. Chem. Soc., 81, 5790 (1959).
25. D. W. A. Sharp and N. Sheppard, J. Chem. Soc., 674 (1957).
26. R. B. Moodie, T. M. Connor, and R. Stewart, Can. J. Chem., 37, 1402 (1959).
27. R. Dehl, W. R. Vaughan, and R. S. Berry, J. Org. Chem., 24, 1616 (1959).
28. R. S. Berry, R. Dehl, and W. R. Vaughan, J. Chem. Phys., 34, 1460 (1961).
29. D. E. O'Reilly and H. P. Leftin, J. Phys. Chem., 64, 1555 (1960).
30. I. I. Schuster, A. K. Colter, and R. J. Kurland, J. Amer. Chem. Soc., 90, 4679 (1968).
31. A. H. Gomes de Mesquita, C. H. MacGillavry, and K. Eriks, Acta Crystallogr., 18, 437 (1965).
32. P. Andersen and B. Klewe, Acta Chem. Scand., 19, 791 (1965).
33. P. Andersen and B. Klewe, Acta Chem. Scand., 21, 2599 (1967).
34. M. Szwarc, Discuss. Faraday Soc., 2, 39 (1947).
35. F. C. Adam and S. I. Weissman, J. Amer. Chem. Soc., 80, 2057 (1958).
36. P. Andersen, Acta Chem. Scand., 19, 629 (1965).
37. J. S. Hyde, R. Breslow, and C. DeBoer, J. Amer. Chem. Soc., 88, 4763 (1966).
38. R. Hoffmann, R. Bissell, and D. G. Farnum, J. Phys. Chem., 73, 1789 (1969).
39. M. Ballester, Pure Appl. Chem., 15, 123 (1967).
40. M. Ballester, J. Riera, J. Castañer, C. Badía, and J. M. Monsó, J. Amer. Chem. Soc., 93, 2215 (1971).
41. J. M. Lehn, Fortschr. Chem. Forsch., 15, 311 (1970).
42. Y. Sasaki, K. Kimura, and M. Kubo, J. Chem. Phys., 31, 477 (1959).
43. W. S. Kelley, L. Monack, P. T. Rogge, R. N. Schwartz, S. P. Varimbi, and R. I. Walter, Justus Liebigs Ann. Chem., 744, 129 (1971).
44. E. L. Muetterties, J. Amer. Chem. Soc., 90, 5097 (1968).
45. E. L. Muetterties, J. Amer. Chem. Soc., 91, 1636 (1969).
46. M. Gielen and C. Depasse-Delit, Theor. Chim. Acta, 14, 212 (1969).
47. M. Gielen, G. Mayence, and J. Topart, J. Organometai. Chem., 18, 1 (1969).
48. M. Gielen and J. Topart, J. Organometai. Chem., 18, 7 (1969).
49. A. K. Colter, I. I. Schuster, and R. J. Kurland, J. Amer. Chem. Soc., 87, 2278 (1965).
50. R. Breslow, L. Kaplan, and D. La-Follette, J. Amer. Chem. Soc., 90, 4056 (1968).
51. B. L. Murr and C. Santiago, J. Amer. Chem. Soc., 90, 2964 (1968).
52. B. L. Murr and L. W. Feller, J. Amer. Chem. Soc., 90, 2966 (1968).
53. H. C. Brown and S. Sujishi, J. Amer. Chem. Soc., 70, 2793 (1948).
54. T. J. Weismann and J. C. Schug, J. Chem. Phys., 40, 956 (1964).
55. W. R. Blackmore and S. C. Abrahams, Acta Crystallogr., 8, 329 (1955).
56. W. R. Blackmore and S. C. Abrahams, Acta Crystallogr., 8, 323 (1955).
57. W. R. Blackmore and S. C. Abrahams, Acta Crystallogr., 8, 317 (1955).
58. D.M.B., McEachern, P.A.F., Lehmann, J. Mol. Struct., (1972), 11, 127
59. V. Cody, W. L. Duax, and D. A. Norton, Chem. Commun., 683 (1971).
60. E. J. W. Whittaker, Acta Crystallogr., 6, 714 (1953).
61. B. Chaudhuri and A. Hargreaves, Acta Crystallogr., 9, 793 (1956).
62. H. G. Norment and I. L. Karle, Acta Crystallogr., 15, 873 (1962).
63. E. B. Fleischer, N. Sung, and S. Hawkinson, J. Phys. Chem., 72, 4311 (1968).
64. G. M. Lobanova, Kristallograñya, 13, 984 (1969).
65. J. Trotter, J. Chem. Soc., 2567 (1962.
66. J. Trotter, Can. J. Chem., 40, 1590 (1962).
67. R. W. G. Wyckoff, “Crystal Structures,” 2nd ed, Vol. 6, Part 2, Interscience, New York, N. Y., 1971, pp 17-78.
68. R. J. LeFévre and J. D. Saxby, J. Chem. Soc. B, 1064 (1966).
69. J. E. Katon, W. R. Feairheller, Jr., and E. R. Lippincott, J. Mol. Spectrosc., 13, 72 (1964).
70. C. W. N. Cumper, J. F. Read, and A. I. Vogel, J. Chem. Soc., 5860 (1965).
71. P. H. Gore, J. A. Hoskins, R. J. W. Le Févre, L. Random, and G. L. D. Ritchie, J. Chem. Soc. B, 741 (1967).
72. W. G. Laidlaw and R. B. Flewwelling, Can. J. Chem., 48, 2158 (1970).
73. K. Higasi and S. Uyeo, Bull. Chem. Soc. Jap., 14, 87 (1939).
74. P.A.F., Lehmann, D.M.B., McEachern, J. Mol. Struct., (1971), 7, 253
75. D.M.B., McEachern, P.A.F., Lehmann, J. Mol. Struct., (1971), 7, 267
76. P.A.F., Lehmann, D.M.B., McEachern, J. Mol. Struct., (1971), 7, 277
77. G. Montaudo, P. Finocchiaro, and S. Caccamese, J. Org. Chem., in press.
78. W. D. Chandler, W. M. Smith, and R. Y. Moir, Can. J. Chem., 42, 2549 (1964).
79. J. J. Bergman and W. D. Chandler, Can. J. Chem., 50, 353 (1972).
80. P. A. Lehman and E. C. Jorgensen, Tetrahedron, 21, 363 (1965).
81. P.A.F., Lehmann, Org. Magn. Resonance, (1970), 2, 467
82. D. A. Bolon, J. Amer. Chem. Soc., 88, 3148 (1966).
83. H. Kessler, A. Rieker, and W. Rundel, Chem. Commun., 475 (1968).
84. G. Montaudo, P. Finocchiaro, E. Trivellone, F. Bottino, and P. Maravigna, Tetrahedron, 27, 2125 (1971).
85. H. Kwart and S. Alekman, J. Amer. Chem. Soc., 90, 4482 (1968).
86. G. Montaudo, S. Caccamese, and P. Finocchiaro, J. Amer. Chem. Soc., 93, 4202 (1971).
87. O. S. Akkerman, Reel. Trav. Chim. Pays-Bas, 89, 673 (1970).
88. A. Hassner and E. G. Nash, Tetrahedron Lett., 525 (1965).
89. A. Mannschreck and L. Ernst, Tetrahedron Lett., 5939 (1968).
90. G. Montaudo and P. Finocchiaro, J. Amer. Chem. Soc., 94, 6745 (1972).
91. B. Meissner and H. A. Staab, Justus Liebigs Ann. Chem., 753, 92 (1971).
92. D. Laur and H. A. Staab, Chem. Ber., 102, 1631 (1969).
93. G. Montaudo, P. Finocchiaro, and P. Maravigna, J. Amer. Chem. Soc., 93, 4214 (1971).
94. K. Maruyama, Bull. Chem. Soc. Jap., 39, 2772 (1966).
95. N. E. Alexandrou, J. Chem. Soc. C, 536 (1969).
96. T. Takeshita and N. Hirota, J. Chem. Phys., 51, 2146 (1969).
97. J. W. Verhoeven, I. P. Dirkx, and Th. J. De Boer, J. Mol, Spectrosc., 36, 284 (1970).
98. G. Montaudo and P. Finocchiaro, Tetrahedron Lett., in press.
99. M. Allen and R. Y. Moir, Can. J. Chem., 37, 1799 (1959).
100. O. S. Akkerman and J. Coops, Reel. Trae. Chim. Pays-Bas, 86, 755 (1967).
101. F. C. Adam and H. R. Falle, Can. J. Chem., 44, 1397 (1966).
102. F. K. Fong, J. Chem. Phys., 40, 132 (1964).