Intramolecular [4 + 2]-Cycloaddition Chemistry of Some 1,3-Dienyl-Substituted Cyclopropenes

Journal of Organic Chemistry

Volumn 55, Issue 8, 1990, Pages 2478-2486

  Padwa, Albert ^a   Kulkarni, Yashwant ^a   Terry, Lenny ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011947021     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00295a043     Document Type: Article

References (125)

1. Padwa, A. Acc. Chem. Res. 1979, 12, 310.
2. Halton, B.; Banwell, M. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chinchester, 1987; Chapter 32.
3. Boger, D. L.; Brotherton, C. F. J. Am. Chem. Soc. 1986,108, 6695, 6713;
4. Tetrahedron 1986, 42, 2777.
5. Halton, B. Ind. Eng. Chem. Prod. Res. Rev. 1980, 19, 349;
6. Chem. Rev. 1973, 73, 113.
7. Billups, W. E. Acc. Chem. Res. 1978, 11, 245.
8. Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978.
9. de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 18, 809.
10. Closs, G. L. Advances in Alicyclic Chemistry; Hart, H., Karabat-sos, G. J., Eds.; Academic Press: New York, 1966; Vol. 1, p 53.
11. Thummel, R. P. Isr. J. Chem. 1982, 22, 11.
12. Padwa, A. Org. Photochem. 1979, 4, 261.
13. Wiberg, K. B.; Fenoglio, R. A. J. Am. Chem. Soc. 1968, 90, 3395.
14. Closs, G. L., Closs, L. A.; Boll, W. E. J. Am. Chem. Soc. 1973, 85, 3796.
15. Deem, M. L. Synthesis 1972, 675.
16. Muller, P.; Rey, M. Helv. Chim. Acta 1981, 64, 354.
17. Albert, R. M.; Butler, G. B. J. Org. Chem. 1977, 42, 674.
18. Galloway, N.; Dent, B. R.; Halton, B. Aust. J. Chem. 1983, 36, 593.
19. Butler, D. N.; Gupta, R. I. Can. J. Chem. 1978, 56, 80.
20. McMullen, G.; Soedelmeier, G.; Hildebrand, R.; Fritz, H.; Prinzbach, H. Tetrahedron Lett. 1978,3847.
21. Buchecker, C. D.; Franck-Neumann, M. Tetrahedron 1977, 33, 751.
22. Buchecker, C. D.; Franck-Neumann, M.; Martina, D. J. Chem. Res. (S) 1978, 79.
23. Sargeant, P. B. J. Am. Chem. Soc. 1969, 91, 3061.
24. Breslow, R.; Ryan, G.; Groves, J. J. J. Am. Chem. Soc. 1970, 92, 998.
25. Law, D. C. F.; Tobey, S. W. J. Am. Chem. Soc. 1968, 90, 2376.
26. Takeuchi, K.; Yokmichi, Y.; Kurosaki, T.; Kimura, Y.; Okamoto, K. Tetrahedron 1979, 35, 949.
27. Reinhoudt, D. N.; Smael, P.; Tilbourg, J. M.; Visser, J. P. Tetrahedron Lett. 1973, 3755.
28. Halton, B.; Battiste, M. A.; Rehberg, R.; Deyrup, C. L.; Brennan, M. E. J. Am. Chem. Soc. 1967, 89, 5964.
29. Martin, H. D.; Kandy, L.; Stusche, D. Tetrahedron Lett. 1977, 3561.
30. LaRochelle, R. W.; Trost, B. M. J. Chem. Soc., Chem. Commun. 1970, 1353.
31. Harthe, K.; Henssen, G.; Kissel, T. Justus Liebigs Ann. Chem. 1980, 1965.
32. Fujise, Y.; Sakaino, M.; Ito, S. Tetrahedron Lett. 1977, 2663.
33. Fuhlhuber, H. D.; Gousetis, G.; Troll, T.; Sauer, J. Tetrahedron Lett. 1978, 3903.
34. Fuhlhuber, H. D.; Gousetis, C.; Sauer, J.; Linder, H. J. Tetrahedron Lett. 1979, 1299.
35. Schuster, H.; Sichert, H.; Sauer, J. Tetrahedron Lett. 1983, 1485.
36. Bradsher, C. K.; Carlson, G. L. B.; Adams, M. G. J. Org. Chem. 1979, 44, 1199;
37. Rigby, J. H.; Kierkus, P. C. J. Am. Chem. Soc. 1989, 111, 4125.
38. Apeloig, Y.; Arad, D.; Kapon, M.; Wallerstein, M. Tetrahedron Lett. 1987, 5917.
39. Matsumoto, K.; Sera, A.; Uchida, T. Synthesis 1985, 1.
40. Kobayashi, Y.; Hanzawa, Y.; Miyashita, W.; Kashiwagi, T.; Na-kano, T.; Kumadaki, I. J. Am. Chem. Soc. 1979,101, 6445.
41. Kobayshi, K.; Nakano, T.; Nakajima, M.; Kumadaki, I. Tetrahedron Lett. 1981,1113.
42. Padwa, A.; Rieker, W. F.; Rosenthal, R. J. J. Org. Chem. 1984,49, 1353.
43. Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63.
44. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10.
45. Taber, D. F. Intramolecular Diels-Alder and Ene Reactions; Springer-Verlag: Berlin, 1984.
46. Ciganik, E. Organic Reactions; John Wiley and Sons, Inc.: New York, 1984; Vol. 32, p 1.
47. Fallis, A. Can. J. Chem. 1984, 62, 183.
48. Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 2.
49. Tufariello, J. J. Acc. Chem. Res. 1979, 12, 396.
50. Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.
51. Confalone, P. N.; Pizzolato, G.; Confalone, D. L.; Uskokovic, M. R. J. Am. Chem. Soc. 1980, 102, 1954.
52. Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554.
53. Baldwin, S. W. Org. Photochem. 1981, 5, 123.
54. Becker, D.; Haddad, N. Org. Photochem. 1989, 10, 1.
55. Padwa, A.; Rieker, W. F.; Rosenthal, R. J. Am. Chem. Soc. 1983, 105, 4446.
56. Padwa, A.; Krumpe, K. E.; Terry, L. W.; Wannamaker, M. W. J. Org. Chem. 1979, 44, 3273.
57. Padwa, A.; Blacklock, T. J.; Loza, R. Tetrahedron Lett. 1979, 1671.
58. Padwa, A.; Blacklock, T. J. J. Am. Chem. Soc. 1977, 99, 2345.
59. Julia, M.; Julia, S.; Guegan, R. Bull. Soc. Chim. Fr. 1960, 1072.
60. Padwa, A.; Blacklock, T. J.; Cordova, D. M.; Loza, R. J. Am. Chem. Soc. 1980, 102, 5648.
61. Dewar, M. J. S.; Pierini, A. B. J. Am. Chem. Soc. 1984,106, 203.
62. Firestone, R. A. Heterocycles 1987, 25, 61.
63. Trifonov, L. S.; Orahovats, A. S. Helv. Chim. Acta 1989, 72, 59.
64. Meinwald, J.; Kapecki, J. A. J. Am. Chem. Soc. 1972, 94, 6236.
65. Nelson, S. F.; Gillespie, J. P. J. Am. Chem. Soc. 1972, 94, 6237.
66. Wittig, G.; Koening, G.; Claus, K. Justus Liebigs Ann. Chem. 1955 593 127
67. Mitchell, R. H.; Sondheimer, F. Tetrahedron Lett. 1968, 2872.
68. Roberts, J. D.; Sharts, C. M. Org. React. 1962, 12, 1.
69. Doering has shown that 2,5-diphenyl-l,5-heptadiene undergoes internal [2 + 2] thermal cycloaddition. See: ref 43. Dewar, M.; Wade, L. E. J. Am. Chem. Soc. 1977, 99, 4419.
70. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970.
71. Kesse, R.; Krebs, E. D. Angew. Chem., Int. Ed. Engl. 1971, 10, 262.
72. Burns, W.; McKervey, M. A. J. Chem. Soc., Chem. Commun. 1974, 858.
73. Lenoir, D. Tetrahedron Lett. 1972, 4049.
74. Gano, J. E.; Eizenberg, L. J. Am. Chem. Soc. 1973, 95, 972.
75. Adams, B. L.; Kovacic, P. J. Am. Chem. Soc. 1973, 95, 8206.
76. Farcasiu, J.; Farcasiu, D.; Conlin, R. T.; Jones, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1973, 95, 8207.
77. Shea, K. J.; Wise, S. Tetrahedron Lett. 1978, 2283.
78. Bartlett, P. D. Science (Washington D.C.) 1968, 159, 833.
79. Huisgen, R. Acc. Chem. Res. 1977, 10, 117.
80. Padwa, A.; Blacklock, T. J. J. Am. Chem. Soc. 1980, 102, 2797; 1985, 107, 1710.
81. Heating a sample of 2 produced 3 (30% yield) together with recovered starting material thereby suggesting an equilibration of both products under the thermal conditions employed. The possibility also, exists that diradical intermediate 8 is directly involved in the cycloaddition of 1 to 2. However, this would require a prior isomerization about the trans double bond in cyclopropene 1. It should be noted that all attempts to detect the cis-vinyl-substituted alkene in the reaction mixture failed. Compound 4 was shown to be stable to the thermal conditions used and no isomerization of the exo-vinyl group to the endo isomer was detected.
82. It should be pointed out that the reaction of 9 could also occur by initial isomerization about the E double bond followed by a [2 + 2]-cycloaddition across the terminal jr-bond. This would result in the formation of cycloadduct i whose NMR properties would be very similar to structure 10. NOE experiments are more consistent with 10 as the structure of the cycloadduct.
83. For reviews, see: Hayakawa, K.; Kanematsu, K. J. Synth. Org. Chem. Jpn. 1986, 44, 109.
84. Craig, D. Chem. Soc. Rev. 1987, 16, 187.
85. DeClercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771.
86. Sternbach, D. D.; Rossana, D. M. J. Am. Chem. Soc. 1982, 10, 5853.
87. Sternbach, D. D. Rossana, D. M. Tetrahedron Lett. 1982, 303.
88. Keay, B. A. J. Chem. Soc., Chem. Commun. 1987, 419.
89. Appendino, G.; Hoflack, F.; DeClercq, P. J.; Chiari, G.; Calleri, M. Tetrahedron 1988,44,4605.
90. Cauwberghs, S.; DeClercq, P. J.; Tinaut, B.; DeClercq, J. P. Tetrahedron Lett. 1988, 2493.
91. Jung, M. E.; Gervay, J. Tetrahedron Lett. 1988, 2429.
92. Fischer, K.; Hunig, S. J. J. Org. Chem. 1987 52, 564.
93. Sternbach, D. D.; Rossana, D. M.; Onan, K. D. Tetrahedron Lett. 1985, 591;
94. J. Org. Chem. 1984, 49, 3428.
95. Burrell, S. J.; Derome, A. E.; Denborough, M. S.; Harwood, L. M.; Lemming, S. A.; Isaacs, N. S. Tetrahedron Lett. 1985, 229.
96. Isaacs, N. S.; Van der Beeke, P. Tetrahedron Lett. 1982, 2147.
97. Henseling, K.; Weyerstahl, P. Chem. Ber. 1975, 108, 2803.
98. Paske, D.; Ringshandl, R.; Sellner, I.; Sichert, H.; Sauer, J. Angew. Chem., Int. Ed. Engl. 1980,19, 456.
99. Huber, F. X.; Sauer, J.; McDonald, W. S.; Noeth, H. Chem. Ber. 1982, 115, 444.
100. Schuster, H.; Sichert, H.; Sauer, J. Tetrahedron Lett. 1983, 1485
101. Farnum, D. G.; Gnandi, M.; Raghu, S.; Reitz, T. J. Org. Chem. 1982, 47, 2598.
102. Snowden, R. L. Tetrahedron Lett. 1981, 97.
103. Paquette, L. A.; Wyvratt, M. J.; Matthew, J. J., Am. Chem. Soc. 1974, 96, 4671.
104. Olsson, T.; Wernerstrom, O. Tetrahedron Lett. 1979, 1721.
105. Kumpp, G. W.; Stapersma, J. J. Chem. Soc., Chem. Commun. 1980, 670.
106. Breitholle, E. G.; Fallis, A. G. J. Org. Chem. 1978, 43, 1964.
107. Landry, D. W. Tetrahedron 1983, 39, 2761.
108. Snowden, R. L. Tetrahedron Lett. 1981, 97.
109. Sternbach, D. D.; Hughes, J. W.; Burdi, D. F.; Banks, B. A. J. Am. Chem. Soc. 1985,107, 2149.
110. Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855.
111. Breslow, R.; Hover, H.; Chang, H. W. J. Am. Chem. Soc. 1962,84, 3168.
112. Calderon, J. L.; Cotton, F. A. Legzdins, P. J. Am. Chem. Soc. 1969, 91, 2528.
113. McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2313.
114. Adam, W.; DeLucchi, O. Angew Chem., Int. Ed. Engl. 1980, 19, 762.
115. Adam, W.; DeLucchi, O.; Erden, I. J. Am. Chem. Soc. 1980, 102, 4806.
116. Adam, W.; DeLucchi, O. Tetrahedron Lett. 1981, 929.
117. Adam, W.; DeLucchi, O.; Hill, K. J. Am. Chem. Soc. 1982, 104, 2934;
118. Chem. Ber. 1982, 115, 1982.
119. Adam, W.; Carballeira, N. J. Am. Chem. Soc. 1984,106, 2874.
120. Billups, W. E.; Lin, L. J. Tetrahedron 1986, 42, 1575.
121. DeBoer, C. D.; Wadsworth, D. H.; Perkins, W. C. J. Am. Chem. Soc. 1973, 95, 861.
122. Wagner, P. J. Acc. Chem. Res. 1971, 4, 168.
123. Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 145.
124. More than likely the conversion of 53 to 54 proceeds via a tri-methylenemethane diradical intermediate.
125. Padwa, A.; Blacklock, T. J.; Getman, D.; Hatanaka, N.; Loza, R. J. J. Org. Chem. 1978, 43, 1481.