Cyclobutene-1,2-diones. A theoretical and spectroscopic study

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6212-6217

  Cerioni, Giovanni ^a   Janoschek, Rudolf ^b   Rappoport, Zvi ^c   Tidwell, Thomas T ^d  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITY OF GRAZ   (Austria)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^d UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000260017     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960484a     Document Type: Article

References (81)

1. (a) Cohen, S.; Lacher, J. R.; Park, J. D. J. Am. Chem. Soc. 1959, 81, 3480.
2. (b) Park, J. D.; Cohen, S.; Lacher, J. R. J. Am. Chem. Soc. 1962, 84, 2919.
3. (c) West, R.; Powell, D. L. J. Am. Chem. Soc. 1963, 85, 2577.
4. (d) Cohen, S.; Cohen, S. G. J. Am. Chem. Soc. 1966, 88, 1533.
5. (e) Schwartz, L. M.; Howard, L. O. J. Phys. Chem. 1971, 75, 1788.
6. (f) Sprenger, H. E.; Ziegenbein, W. Angew. Chem., Int. Ed. Engl. 1968, 7, 530.
7. (a) Ried, W.; Schmidt, A. H. Angew. Chem., Int. Ed. Engl. 1972, 11, 997.
8. (b) Schmidt, A. H.; Ried, W. Synthesis 1978, 1.
9. (c) Knorr, H.; Ried, W. Synthesis 1978, 649.
10. (d) Schmidt, A. H.; Ried, W. Synthesis 1978, 869.
11. (e) Schmidt, A. H. Synthesis 1980, 961.
12. (a) Moore, H. W.; Yerxa, B. R. Adv. Strain Org. Chem. 1995, 4, 81.
13. (b) Lee, K. H.; Moore, H. W. J. Org. Chem. 1995, 60, 735.
14. (c) Koo, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389.
15. (d) Danheiser, R. L.; Casebier, D. S.; Huboux, A. H. J. Org. Chem. 1994, 59, 4844.
16. (e) Yamamoto, Y.; Ohno, M.; Eguchi, S. J. Am. Chem. Soc. 1995, 117, 9653.
17. (a) Cole, R. J.; Kirksey, J. W.; Cutler, H. G.; Doupnik, B. L.; Peckham, J. C. Science 1973, 179, 1324.
18. (b) Tietze, L. F.; Arlt, M.; Beller, M.; Glüsenkamp, K. H.; Jähde, E.; Rajewsky, M. F. Chem. Ber. 1991, 124, 1215.
19. (a) Tidwell T. T. Ketenes; Wiley: New York, 1995.
20. (b) McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1994, 116, 7233.
21. (c) Allen, A. D.; Lai, W.-Y.; Ma, J.; Tidwell, T. T. J. Am. Chem. Soc. 1994, 116, 2625.
22. (d) Allen, A. D.; Colomvakos, J. D.; Egle, I.; Lusztyk, J.; McAllister, M. A.; Tidwell, T. T.; Wagner, B. D.; Zhao, D.-C J. Am. Chem. Soc. 1995, 117, 7552.
23. (a) Maier, G.; Reisenauer, H. P.; Sayrac, T. Chem. Ber. 1982, 115, 2192.
24. (b) Hochstrasser, R.; Wirz, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 181.
25. (a) Chen, H.; Law, K.-Y.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7257.
26. (b) McKerrow, A. J.; Buncel, E.; Kazmaier, P. M. Can. J. Chem. 1995, 73, 1605.
27. (c) Keil, D.; Hartmann, H. Liebigs Ann. 1995, 979.
28. (d) Law, K.-Y. Chem. Rev. 1993, 93, 449.
29. (e) Gheorghiu, M. D.; Tidwell, T. T. 208th National American Chemical Society Meeting, August 21-25, 1994, Washington, D.C.; Abstract COMP, 0083.
30. (a) West, R.; Ed. Oxocarbons; Academic Press: New York, 1980.
31. (b) Cava, M. P.; Mitchell, M. J. Cyclobutadiene and Related Compounds; Academic Press: New York, 1967.
32. Rathna, A.; Chandrasekhar, J. J. Chem. Soc., Perkin Trans. 2 1991, 1661.
33. (a) Dahn, H.; Ung-Truong, M.-N. Helv. Chim. Acta 1987, 70, 2130 and references therein.
34. (b) Cerioni, G.; Culeddu, N.; Saba, A. J. Phys. Org. Chem. 1992, 5, 424 and references therein.
35. (c) Cerioni, G.; Culeddu, N.; Saba, A. Magn. Reson. Chem. 1993, 31, 829 and references therein.
36. Boykin, D. W.; Ed. O-17 NMR Spectroscopy in Organic Chemistry CRC Press: Boca Raton, FL, 1991.
37. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1, Wisconsin, 1988.
38. GAUSSIAN 94, Revision B.3, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc, Pittsburgh, PA, 1995.
39. MacDonald, D. J. J. Org: Chem. 1968, 33, 4559.
40. Darken, L. S. J. Am. Chem. Soc. 1941, 63, 1007.
41. Pinching, G. D.; Bates, R. G. J. Res. Nat. Bur. Stand., A 1948, 40, 405.
42. Janoschek, R. Z. Anorg. Allg. Chem. 1992, 616, 101.
43. (a) Boykin, D. W.; Baumstark, A. L. in ref 11, Chap. 8, p 217 and references therein.
44. (b) Delseth, C.; Nguyen, T. T.-T.; Kintzinger, J.-P. Helv. Chim. Acta 1980, 63, 498.
45. (c) Boykin, D. W. Spectrochim. Acta 1991, 47A, 323.
46. Gerothanassis, I. P.; Hunston, R.; Lauterwein, J. Helv. Chim. Acta 1982, 65, 1764 and ref 39 therein (Carrupt, P.-A.; Gerothanassis, I. P.; Lauterwein, J. Unpublished results).
47. Gerothanassis, I. P.; Hunston, R.; Lauterwein, J. Helv. Chim. Acta 1982, 65, 1764 and ref 39 therein (Carrupt, P.-A.; Gerothanassis, I. P.; Lauterwein, J. Unpublished results).
48. Macintyre, W. M.; Werkema, M. S. J. Chem. Phys. 1964, 42, 3563.
49. Monti, D.; Orsini, F.; Ricca, G. S. Spectrosc. Lett. 1986, 19, 91.
50. Balakrishnan, P.; Baumstark, A. L.; Boykin, D. W. Org. Magn. Reson. 1984, 22, 753.
51. Baumstark, A. L.; Balakrishnan, P.; Dotrong, M.; McCloskey, C. J.; Oakley, M. G.; Boykin, D. W. J. Am. Chem. Soc. 1987, 109, 1059.
52. Baltzer, L.; Becker, E. D. J. Am. Chem. Soc. 1983, 105, 5730.
53. Boykin, W. D.; Kumar, A.; Shevchenko, S. M. Magn. Reson. Chem. 1992, 30, 16.
54. (a) Kintzinger, J.-P.; Delseth, C.; Nguyen, T. T.-T. Tetrahedron 1980, 36, 3431.
55. (b) Kalabin, G. A.; Kushnarev, D. F.; Valeyev, R. B.; Trofimov, B. A.; Fedotov, M. A. Org. Magn Reson. 1982, 18, 1.
56. Chandrasekaran, S. in ref 11, Chap. 7.
57. Thorpe, J. E. J. Chem. Soc. (B) 1968, 435.
58. Boykin, D. W.; Baumstark, A. L. in ref 11, Chap. 8, pp 208-11 and references therein.
59. Dehmlow, E. V.; Zeisberg, R.; Dehmlow, S. S. Org. Magn Reson. 1975, 7, 418.
60. Orendt, A. M.; Facelli, J. C.; Beeler, A. J.; Reuter, K.; Horton, W. J.; Cutts, P.; Grant, D. M.; Michl, J. J. Am. Chem. Soc. 1988, 110, 3386.
61. Allen, A. D.; Egle, I.; Janoschek, R.; Liu, H. W.; Ma, J.; Marra, R. M.; Tidwell, T. T. Chem. Lett. 1996, 45 and references therein.
62. Lambert, J. B.; Singer, R. A. J. Am. Chem. Soc. 1992, 114, 10246. J. Am. Chem. Soc. 1995, 117, 2122.
63. Lambert, J. B.; Singer, R. A. J. Am. Chem. Soc. 1992, 114, 10246. J. Am. Chem. Soc. 1995, 117, 2122.
64. Sakurai, H.; Kamiyama, Y.; Mikoda, A.; Kobayashi, T.; Sasaki, K.; Nakadaira, Y. J. Organomet. Chem. 1980, 201, C14.
65. Bassindale, A. R.; Taylor, P. G. in The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds. Wiley: New York, 1989; Part 2, Chap. 14, p 902.
66. (a) Dahn, H.; Péchy, P.; Toan, V. V. Magn. Reson. Chem. 1990, 28, 883.
67. (b) Chimichi, S.; Mealli, C. J. Mol. Struct. 1992, 271, 133.
68. (c) Dahn, H.; Péchy, P.; Bestmann, H. J. J. Chem. Soc., Perkin Trans. 2 1993, 1497.
69. Karplus, M.; Pople, J. A. J. Chem. Phys. 1963, 38, 2803.
70. Zhao, D.-C.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 10980.
71. Blomquist, A. T.; Vierling, R. A. Tetrahedron Lett. 1961, 655.
72. (a) Boykin, D. W. Spectrosc. Lett. 1990, 23, 1133.
73. (b) Dahn, H.; Péchy, P.; Toan, V. V. Angew. Chem., Int. Ed. Engl. 1990, 29, 647.
74. (c) Dahn, H.; Péchy, P. J. Chem. Soc., Perkin Trans. 2 1991, 1721.
75. (d) Dahn, H.; Péchy, P J. Chim. Phys. 1992, 89, 1683.
76. Cerioni, G.; Plumitallo, A.; Frey, J.; Rappoport, Z. Magn. Reson. Chem. 1995, 33, 874.
77. Delseth, C.; Kintzinger, J.-P. Helv. Chim. Acta 1976, 59, 466.
78. Blomquist, A. T.; LaLancette, J. Tetrahedron Lett. 1961, 655.
79. DeSelms, R. C.; Fox, C. J.; Riordan, R. C. Tetrahedron Lett. 1970, 781.
80. Schmidt, A. H.; Kunz, C.; Debo, M.; Mora-Ferrer, J. Synthesis 1990, 819.
81. Green, B. R.; Neuse, E. W. Synthesis 1974, 46.