Tetraacylethenes as dienophiles and hetero dienes in two-step Diels- Alder reactions

European Journal of Organic Chemistry

Volumn , Issue 12, 1999, Pages 3343-3351

  Quast, Helmut ^a   Seefelder, Maximilian ^a   Ivanova, Svetlana ^a   Heubes, Markus ^a   Peters, Eva Maria ^b   Peters, Karl ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

C C coupling; Cycloadditions; Dehydrogenations; Electron deficiency; Isomerisations; Oxidations; Zwitterionic intermediates

Indexed keywords

ETHYLENE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ISOMERISM; SPECTRAL SENSITIVITY;

EID: 0032726378     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3343::AID-EJOC3343>3.0.CO;2-S     Document Type: Article

References (81)

1. [1a] D. N. Dhar, Chem. Rev. 1967, 67, 611-622.
2. [1b] E. Ciganek, W. J. Linn, O. W. Webster, in: The Chemistry of the Cyano Group (Ed.: Z. Rappoport), Wiley, New York, 1970, pp. 449-453.
3. [1c] A. J. Fatiadi, Synthesis 1986, 249-284.
4. [2a] K. Alder, H. F. Rickert, Ber. Dtsch. Chem. Ges. 1939, 72, 1983-1992.
5. [2b] J.-L. Ripoll, Bull. Soc. Chim. Fr. 1974, 2567-2571.
6. [2c] K. Weinges, K. Klessing, R. Kolb. Chem. Ber. 1973, 106, 2298-2304.
7. [2d] K. Weinges, K. Klessing, H. Baake, Chem. Ber. 1976, 109, 796-798.
8. [2e] K. H. Ang, S. Braese, A. G. Steinig, F. E. Meyer, A. Liebaria, K. Voigt, A. de Meijere, Tetrahedron 1996, 52, 11503-11528.
9. [2f] W. Zeslawski, J. Barańska, M. Jamrozik, J. Jamrozik, Monatsh. Chem. 1997, 128, 389-394.
10. G. Adembri, F. De Sio, R. Nesi, M. Scotton, J. Chem. Soc. C 1970, 1536-1540.
11. A. M. Celli, L. R. Lampariello, S. Chimichi, R. Nesi, M. Scotton, Can. J. Chem. 1982, 60, 1327-1332.
12. [5a] B. A. Arbuzow, N. P. Bogonoszewa, Izv. Akad. Nauk. SSSR. Ser. Khim. 1954, 837-845; Chem. Abstr. 1955, 49, 13940g.
13. [5a] B. A. Arbuzow, N. P. Bogonoszewa, Izv. Akad. Nauk. SSSR. Ser. Khim. 1954, 837-845; Chem. Abstr. 1955, 49, 13940g.
14. [5b] Y. Hayasi, T. Okada, M. Kawanisi, Bull. Chem. Soc. Jpn. 1970, 43, 2506-2511.
15. [5c] M. P. Cava, M. Behforouz, G. E. M. Husbands, M. J. Srinivasan, J. Am. Chem. Soc. 1973, 95, 2561-2564.
16. [5d] H. W. VandenBorn, D. H. Evans, J. Am. Chem. Soc. 1974, 96, 4296-4301.
17. [5e] R. M. Wilson, A. C. Hengge, A. Ataei, D. M. Ho, J. Am. Chem. Soc. 1991, 113, 7240-7249.
18. L. Lepage, Y. Lepage, Synthesis 1983, 1018-1019.
19. Reviews on propellanes: [7a] D. Ginsburg, Acc. Chem. Res. 1969, 2, 121-128.
20. [7b] D. Ginsburg, Top. Curr. Chem. 1986, 137, 1-17.
21. [7c] Y. Tobe, in: Carbocyclic Cage Compounds: Chemistry and Applications (Eds.: E. Osawa, O. Yonemitsu). 1st ed.. VCH Publishers, New York, 1992.
22. W. J. Middleton, R. E. Heckert, E. L. Little, C. G. Krespan, J. Am. Chem. Soc. 1958, 80, 2783-2788.
23. D. A. White, J. Electrochem. Soc. 1977, 124, 1177-1184.
24. [10a] A. T. Nielsen, W. J. Houlihan, Org. React. 1968, 16, 49-56.
25. -For more recent examples see: [10b] D. Pauley, F. Anderson, T. Hudlicky, Org. Synth. Coll. Vol. 1993, 8, 208-209.
26. [10c] H. Stetter, H. Kuhlmann, W. Haese, Org. Synth. Coll. Vol. 1993, 8, 620-623.
27. R. G. Charles, Org. Synth. Coll. Vol. 1963, 4, 869-871.
28. J. R. Cannon, V. A. Patrick, C. L. Raston, A. H. White, Aust. J. Chem. 1978, 31, 1265-1283.
29. J. Dannheim, W. Grahn, H. Hopf, C. Parrodi, Chem. Ber. 1987, 120, 871-872.
30. [14a] B. B. Corson, W. L. Benson, Org. Synth. Coll. Vol. 1943, 2, 273-275.
31. [14b] J. C. Le Menn, J. Sarrazin, A. Tallec, Bull. Soc. Chim. Fr. 1991, 128, 562-565.
32. L. Y. Cho, J. R. Romero, Tetrahedron Lett. 1995, 36, 8757-8760.
33. For the same cyclisation of 10 in the presence of strong acids see: [16a] C. U. Zanetti, Gazz. Chim. Ital. 1893, 23 II, 299-312.
34. [16b] S. P. Mulliken, Am. Chem. J. 1893, 15, 523-533.
35. [16c] T. Rull, G. Le Strat, Bull. Soc. Chim. Fr. 1975, 1371-1374.
36. [16d] E. P. Olekhnovich, S. L. Boroshko, G. S. Borodkin, I. V. Korobka, V. I. Minkin, L. P. Olekhnovic, Russ. J. Org. Chem. 1996, 32, 859-864.
37. G. Adembri, P. Dapporto, D. Donati, L. R. Lampariello, P. Paoli, M. Scotton, A. Sega, J. Chem. Res. (S) 1991, 338-339.
38. [18a] R. Antonioletti, M. D'Auria, A. De Mico, G. Piancatelli, A. Scettri, Synthesis 1984, 280-281.
39. [18b] Review: G. Piancatelli, A. Scettri, M. D'Auria, Synthesis 1982, 245-258.
40. Reviews: [19a] A. J. Fatiadi, Synthesis 1976, 65-104.
41. [19b] A. J. Fatiadi, Synthesis 1976, 133-167.
42. R. A. Sheldon, J. K. Kochi, Org. React. 1972, 19, 279-421.
43. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
44. D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu, Jr., A. I. Meyers, J. Org. Chem. 1979, 44, 497-501, and references cited therein.
45. [23a] G. W. Thompson, L. T. Ockerman, J. M. Schreyer, J. Am. Chem. Soc. 1951, 73, 1379-1381.
46. [23b] Y. Tsuda, S. Nakajima, Chem. Lett. 1978, 1397-1398.
47. [24a] D. Walker, J. D. Hiebert, Chem. Rev. 1967, 67, 153-195.
48. [24b] J. S. Pizey, Synthetic Reagents, vol. 3, Wiley, New York, 1977, pp. 193-225.
49. [24c] D. R. Buckle, I. L. Pinto, in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), vol. 7, Pergamon, Oxford, 1991, pp. 135-139.
50. [25a] H. Firouzabadi, E. Ghaderi, Tetrahedron Lett. 1978, 9, 839-840.
51. [25b] H. Firouzabadi, Z. Mostafavipoor, Bull. Chem Soc. Jpn. 1983, 56, 914-917.
52. [26a] J. P. Schaefer, P. J. Wheatley, J. Chem. Soc. A 1966, 528-532.
53. [26b] L. F. Power, K. E. Turner, F. H. Moore, Inorg. Nucl. Chem. Lett. 1972, 8, 313-315.
54. [26c] L. F. Power, K. E. Turner, F. H. Moore, J. Cryst. Mol. Struct. 1975, 5, 59-66.
55. E. Fischer, C. Bülow, Ber. Dtsch. Chem. Ges. 1885, 18, 2131-2138.
56. J. S. Oh, J. C. Bailar, Jr., J. Inorg. Nucl. Chem. 1962, 24, 1225-1234.
57. J. R. Cannon, V. A. Patrick, A. H. White, Aust. J. Chem. 1986, 11, 1811-1821.
58. A. Wu, Y. Zhao, N. Chen, X. Pan, Synth. Commun. 1997, 27, 331-336.
59. M. Laćan, I. Tabaković, M. Vukićević, Croat. Chim. Acta 1973, 45, 465-474.
60. H. Ohmori, H. Maeda, M. Tamaoka, M. Masui, Chem. Pharm. Bull. 1988, 36, 613-620.
61. T. Suehiro, Nippon Kagaku Zasshi 1958, 79, 457-461; Chem. Abstr. 1960, 54, 4486d.
62. T. Suehiro, Nippon Kagaku Zasshi 1958, 79, 457-461; Chem. Abstr. 1960, 54, 4486d.
63. R. M. Moriarty, R. K. Vaid, V. T. Ravikumar, B. K. Vaid, T. E. Hopkins, Tetrahedron 1988, 44, 1603-1607.
64. L. Wolf, C. Tröltzsch, J. Prakt. Chem. 1962, 17, 69-77.
65. N. M. D. Brown, P. Bladon, J. Chem. Soc. A 1969, 526-532.
66. Recent review on oxa Diels - Alder reactions with 1-oxa-1,3-butadienes: L. F. Tietze, G. Kettschau, Top. Curr. Chem. 1997, 189, 26-45.
67. E. Beckmann, N. Bahr, H. Prinzbach, G. Rihs, Tetrahedron Lett. 1990, 31, 1125-1128.
68. G. Adembri, D. Donati, R. Cini, R. Nesi, M. Scotton, Can. J. Chem. 1980, 58, 1645-1650.
69. G. Adembri, R. Nesi, M. Section, Tetrahedron Lett. 1977, 3961-3964.
70. G. Adembri, R. Cini, P. Orioli, R. Nesi, M. Scotton, J. Chem. Soc., Perkin Trans. 2 1979, 903-906.
71. A. G. Yurchenko, A. B. Kyrij, I. R. Likhotvorik, N. N. Melnik, P. Zaharzh, V. V. Bzhezovski, A. O. Kushko, Synthesis 1991, 393-394.
72. P. D. Bartlett, A. S. Wingrove, R. Owyang, J. Am. Chem. Soc. 1968, 90, 6067-6070.
73. F. Kataoka, N. Shimizu, S. Nishida, J. Am. Chem. Soc. 1980, 102, 711-716.
74. F. Jensen, C. S. Foote, J. Am. Chem. Soc. 1987, 109, 6376-6385.
75. [46a] M. Heuschmann, Chem. Ber. 1988, 121, 39-49.
76. [46b] K.-P. Hartmann, M. Heuschmann, Angew. Chem. 1989, 101, 1288-1290; Angew. Chem. Int. Ed. 1989, 28, 1267-1268.
77. [46b] K.-P. Hartmann, M. Heuschmann, Angew. Chem. 1989, 101, 1288-1290; Angew. Chem. Int. Ed. 1989, 28, 1267-1268.
78. A. M. Celli, L. R. Lampariello, S. Chimichi, R. Nesi, M. Scotton, Gazz. Chim. Ital. 1983, 113, 427-431.
79. H. Saltzman, J. G. Sharefkin, Org. Synth. Coll. Vol. 1973, 5, 658-659.
80. G. M. Sheldrick, University of Göttingen, unpublished.
81. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-125740 (27), -125741 (25), -125742 (19), -125743 [(E)-7b]. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: internat, code + 44-1223/336-033, E-mail: deposit@ccdc.cam.ac.uk].