Reaction of 4-Phenyl-1,2,4-triazoline-3,5-dione with Substituted Butadienes: A Nonconcerted Diels-Alder Reaction

Journal of the American Chemical Society

Volumn 109, Issue 21, 1987, Pages 6376-6385

  Jensen, Frank ^a   Foote, Christopher S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845281275     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00255a024     Document Type: Article

References (57)

1. Bartlett, P. D.; Mallet, J. J. B. J. Am. Chem. Soc. 1976, 98, 143. Victor, M. J. Org. Chem. 1974, 39, 3179, 3181. Bartlett, P. D.; Lawrence, K. M.; Seidel, B. J. Am. Chem. Soc. 1964, 86, 616. Bartlett, P. D. Ot. Rev. Chem. Soc. 1970, 24, 473.
2. For a review of the mechanism of the Diels-Alder reactions, see: Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
3. Little, J. C. J. Am. Chem. Soc. 1965, 87, 4020.
4. Gompper, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 312.
5. Burrage, M. E.; Cookson, R. C.; Gupte, S. S.; Stevens, D. R. J. Chem. Soc., Perkin Trans. 2 1975, 1325 and references therein. Toong, Y. C.; Borden, W. T.; Gold, A. Tetrahedron Lett. 1975, 1549. Konovalov, A. I.; Breus, I. P.; Sharagin, I. A.; Kiselev, V. D. J. Org. Chem. USSR (Engl. Transl.) 1979, 15, 315. Sauer, J.; Schroder, B. Chem. Ber. 1967, 100, 678. Cookson, R. C.; Gilani, S. S.; Stevens, D. R. J. Chem. Soc. C 1967, 1905. Scharf, H. D.; Plum, H.; Fleischhauer, J.; Schleker, W. Chem. Ber. 1979. 112, 862.
6. For a recent review of reactions of azodicarboxyl compounds, see: Moody, C. J. Adv. Heterocycl. Chem. 1982, 30, 1.
7. Cheng, C. C.; Seymour, C. A.; Petti, M. A.; Greene, F. D.; Blount, J. F. J. Org. Chem. 1984, 49, 2910.
8. Adam, W.; Carballeira, N. J. Am. Chem. Soc. 1984, 106, 2874. Stephenson, L. M.; Mattern, D. L. J. Org. Chem. 1976, 41, 3614. Thaler, W. A.; Franzus, B. J. Org. Chem. 1964, 29, 2226. Pasto, D. J.; Chen, A. J. Am. Chem. Soc. 1971, 93, 2562. Heise, I.; Leitich, J. Chem. Ber. 1985, 118, 332. Adam, W.; Durr, H.; Paluy, K. H.; Lucchi, O. D.; Peters, E. M.; Peters, K.; Rebollo, H.; von Schnering, H. G. J. Org. Chem. 1984, 49, 2333. Osinichi, S.; Leong, K.; Matyjaszewski, K.; Butler, G. B. J. Org. Chem. 1980, 45, 3467. Hoye, T. R.; Bottorff, K. J.; Caruso, A. J.; Dellaria, J. F. J. Org. Chem. 1980, 45, 4287. Ohashi, S.; Butler, G. B. J. Org. Chem. 1980, 45, 3472. Huisgen, R.; Konz, W. E.; Schnegg, U. Angew. Chem., Int. Ed. Engl. 1972, 8, 715. Adam, W.; Griesbeck, A.; Klarner, K. G.; Schroer, D. Angew. Chem. 1986, 98, 1006.
9. For a review of the ene reaction, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556.
10. Frimer, A. A. Chem. Rev. 1979, 79, 358.
11. Seymour, C. A.; Greene, F. D. J. Am. Chem. Soc. 1980, 102, 6384.
12. Orfanopoulos, M.; Foote, C. S.; Smonou, I. Tetrahedron Lett. 1987, 15.
13. Stephenson, L. M. Tetrahedron Lett. 1980, 1005. Grdina, B., Sr.; Orfanopoulos, M.; Stephenson, L. M. J. Am. Chem. Soc. 1979, 101, 3111.
14. Orfanopoulos, M.; Foote, C. S. Free Radical Res. Commun. 1987, 2, 321.
15. Stephenson, L. M.; Grdina, M. J.; Orfanopoulos, M. Acc. Chem. Res. 1980, 13, 419.
16. Nelsen, S. F.; Kapp, D. L. J. Am. Chem. Soc. 1985, 107, 5548.
17. Wagener, K. B.; Turner, S. R.; Butler, G. B. J. Org. Chem. 1972, 37, 1454.
18. Adam, W.; Lucchi, O. D. Tetrahedron Lett. 1981, 929.
19. Koerner, V.; Gustorf, E.; White, D. V.; Kim, B.; Hess, D.; Leitich, J. J. Org. Chem. 1970, 35, 1155.
20. Firl, J.; Sommer, S. Tetrahedron Lett. 1970, 1925, 1929.
21. Koerner, V.; Gustorf, E.; White, D.; Leitich, J.; Henneberg, D. Tetrahedron Lett. 1969, 3113.
22. Hoffmann, R.; Woodward, R. B. J. Am. Chem. Soc. 1965, 87, 2046. Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. Hoffmann, R.; Woodward, R. B. Angew. Chem. 1969, 81, 797.
23. Turner, S. R.; Guilbault, L. J.; Butler, G. B. J. Org. Chem. 1971, 36, 2838.
24. Hall, J. H.; Jones, M. L. J. Org. Chem. 1983, 48, 822.
25. Firl, J.; Sommer, S. Tetrahedron Lett. 1979, 4713. (26) For other reactions involving polar intermediates, see: Gassman, P. G.; Hoye, R. C. J. Am. Chem. Soc. 1981, 103, 2496. Adam, W.; Lucchi, O. D.; Peters, K.; Peters, E. M.; von Schnering, H. G. J. Am. Chem. Soc. 1982, 104, 161. Hall, J. H.; Wojciechowska, M. J. Org. Chem. 1979, 44, 38. Amey, R. L.; Smart, B. E. J. Org. Chem. 1981, 46, 4090. Ohashi, S.; Rych, W. E.; Butler, G. B. J. Org. Chem. 1981, 46, 614.
26. Gillis, B. T.; Hagarty, J. D. J. Org. Chem. 1967, 32, 330.
27. Clennan, E. L.; L'Esperance, R. J. Am. Chem. Soc. 1985, 107, 5178. See also: Clennan, E. L.; Lewis, K. K. J. Am. Chem. Soc. 1987, 109, 2475.
28. Cookson, K. C.; Gupte, S. S.; Stevens, L. R. D.; Watts, C. T. Org. Synth. 1971, 51, 121.
29. Product 1 has been reported previously: Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. Tetrahedron Lett. 1962, 615. Sceradsky, T.; Moshenberg, R. J. Org. Chem. 1985, 50, 5604, and ref 5 and 27. Products analogous to 2 and 3 using dimethyl azodicarboxylate instead of PTAD have been reported previously: Dervan, P. B.; Uyerhara, T. J. Am. Chem. Soc. 1976, 98, 1262.
30. Huebner, C. F.; Strachan, P. L.; Donoghue, E. M.; Cahoon, N.; Dorfman, L.; Margerison, R.; Wenkert, E. J. Org. Chem. 1967, 32, 1126. Koerner v. Gustorf, E.; White, D.; Leitich, J. Tetrahedron Lett. 1969, 3109. Huebner, C. F.; Donoghue, E. M.; Novak, C. J.; Dorfman, L.; Wenkert, E. J. Org. Chem. 1970, 35, 1149.
31. Lippert, E.; Prigge, H. Ber. Bunsen-Ges. Phys. Chem. 1963, 67, 415. Foote, C. S. Tetrahedron Lett. 1963, 579.
32. Pasto, D. J.; Chen, A. F. T. Tetrahedron Lett. 1972, 2995.
33. Sasaki, T.; Eguchi, S.; Hirako, Y. Tetrahedron 1976, 32, 437.
34. Hamersma, J. W.; Snyder, E. L. J. Org. Chem. 1965, JU, 3985. van Tamelen, E. E.; Dewey, R. S.; Timmens, R. J. J. Am. Chem. Soc. 1961, 83, 3725.
35. Gollnick, K.; Griesbeck, A. Tetrahedron 1984, 40,3235.
36. The reaction between MeTAD and cis- and trans-2-butene has been reported earlier: Pirkle, W. H.; Stickler, J. C. J. Chem. Soc., Chem. Commun. 1967, 760.
37. Franzus, B. J. Org. Chem. 1963, 28, 2954.
38. Manring, L. E.; Kanner, R. C.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4707. Manring, L. E.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4710. Zhang, J.; Foote, C. S. Tetrahedron Lett. 1986, 27, 6153. Burns, P. A.; Foote, C. S. J. Am. Chem. Soc. 1974, 96, 4339. Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 2655, 3396, 7771. Hatsui, T.; Takeshita, H. Bull. Soc. Chem. Jpn. 1980, 53, 2655. Hasty, N. M.; Kearns, D. R. J. Am. Chem. Soc. 1973, 95, 3380. Gollnick, K.; Kuhn, H. J. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic: New York, 1979.
39. For a discussion, see: Yamaguchi, K.; Ikeda, Y.; Fueno, T. Tetrahedron 1985, 41, 2099.
40. Bollinger, J. M.; Brinich, J. M.; Olah, G. A. J. Am. Chem. Soc. 1970, 92, 4025, structure 37. Deno, N. C.; Haddon, R. C.; Nowak, E. N. J. Am. Chem. Soc. 1970. 92. 6691.
41. For the parent allyl radical the barrier is 15.7 kcal/mol and for the 1,1-dimethyl-substituted case, >14 kcal/mol. Korth, H. G.; Trill, H.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483. Krusic, P. J.; Meakin, P.; Smart, B. E. J. Am. Chem. Soc. 1974, 96, 6211.
42. For a review of diazetidine chemistry, see: Richter, R.; Ulrich, H. In Small Ring Heterocycles, Part 2 1983, 443.
43. Eisch, J. J.; Husk, G. R. J. Org. Chem. 1966, 31, 589. Drexler, J.; Lindermayer, R.; Hassan, M. A.; Sauer, J. Tetrahedron Lett. 1985, 2555, 2559. Kataoka, F.; Shimizu, N.; Nishida, S. J. Am. Chem. Soc. 1980, 102, 711.
44. Allinger, N. L.; Yuh, Y. QCPE 1980, 12, 395. Burkert, U.; Allinger, N. L. Molecular Mechanics; American Chemical Society: Washington, DC, 1982.
45. Doring, C. E.; Hauthal, H. G. J. Prakt. Chem. 1964, 24, 27. (57) Bell, R. P. Proc. R. Soc. London, A 1936, 154, 414. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1938, 34, 49; 1937, 33, 448; 1935, 31, 875; 1938, 34, 11; 1936, 32, 1333.
46. Franzus, B.; Surridge, J. H. J. Org. Chem. 1962, 27, 1951. Gillis, B. T.; Beck, P. E. J. Org. Chem. 1963, 28, 3177. Gillis, B. T.; Beck, P. E. J. Org. Chem. 1962, 27, 1947. Huisgen, R.; Pohl, H. Chem. Ber. 1960, 93, 527.
47. Schenck, G. O.; Hopp, H. R.; Kim, B.; Koerner, V.; Gustorf, E. Z.; Naturforsch, B.; Angew. Chem., Org. Chem. 1965, 20B, 637. Schenck, G. O.; Engelhard, N. Angew. Chem. 1956, 68, 71.
48. Askani, R. Chem. Ber. 1965, 98, 2551.
49. Huisgen, R. Acc. Chem. Res. 1977, 10, 117, 199. Blomquist, A. T.; Meinwald, Y. C. J. Am. Chem. Soc. 1959, 81, 667. Huisgen, R.; Ortega, J. P. Tetrahedron Lett. 1978, 3975. Sasaki, T.; Eguchi, S.; Sugimoto, M.; Hibi, F. J. Org. Chem. 1972, 37, 2317. Steward, C. A. J. Am. Chem. Soc. 1962, 84, 117. Williams, J. K.; Wiley, D. W.; McKusick, B. C. J. Am. Chem. Soc. 1962, 84, 2210. Huisgen, R.; Schug, R. J. Am. Chem. Soc. 1976, 98, 7819. Herges, R.; Ugi, I. Chem. Ber. 1986, 119, 829. Steward, C. A., Jr. J. Org. Chem. 1963, 28, 3320. Weber, W.; Erden, I.; Meijere, A. Angew. Chem., Int. Ed. Engl. 1980, 19, 387. Gotoh, T.; Padias, A. B.; Hall, K. K., Jr. J. Am. Chem. Soc. 1986, 108, 4920. (1) Shimizu, N.; Fuioka, T.; Ishizuka, S.; Tsuji, T.; Nishida, S. J. Am. Chem. Soc. 1977, 99, 3973.
50. Clennan, E. L.; Earlywine, A. D. J. Am. Chem. Soc., submitted.
51. Morris, G. A.; Freeman, R. J. Am. Chem. Soc. 1979, 101, 760.
52. Mints, M. J.; Walling, C. Organic Syntheses; Wiley; New York, 1973; Collect. Vol. V.,p 184.
53. Carreira, L. A. J. Chem. Phys. 1975, 62, 385.
54. Zurn, V.; Schwarc, W.; Rozdzinski, W.; Schmidt, A. Z.; Naturforsch, B.; Anorg. Chem., Org. Chem. 1982, 37B, 81. See also: Wadsworth, W. S.; Emmons, W. D. J. Org. Chem. 1967, 32, 1279, and ref 69.
55. Ried, W.; Lim, S. H. Liebigs. Ann. Chem. 1973, 1141. Bethauser, W.; Regitz, M.; Theis, W. Tetrahedron Lett. 1981, 2535.
56. Yamaguchi, K.; Yabushita, S.; Fueno, T. Chem. Phys. Lett. 1981, 78, 572.
57. Hotokka, M.; Roos, B.; Siegbahn, P. S. J. Am. Chem. Soc. 1983, 105, 5263.