Ketene is a dienophile for [4 + 2] (Diels-Alder) reactions across its C=O bond

Journal of the American Chemical Society

Volumn 118, Issue 27, 1996, Pages 6518-6519

  Yamabe, Shinichi ^a   Dai, Tatsuo ^a   Minato, Tsutomu ^b   Machiguchi, Takahisa ^c   Hasegawa, Toshio ^c  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

^b NARA UNIVERSITY   (Japan)

^c SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029934693     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960083c     Document Type: Article

References (42)

1. Dedicated to Professor Emeritus Rolf Huisgen, Universität München, on the occasion of his 76th birthday and lifelong career in organic chemistry. For his biography and research history, see: Huisgen, R. The Adventure Playground of Mechanisms and Novel Reactions. In Profiles, Pathways, and Dreams: Autobiographies of Eminent Chemists; Seeman, J. I., Ed.; American Chemical Society: Washington, DC, 1994.
2. For excellent reviews, see: (a) Hyatt, J.; Raynolds, R. W. Org. React. 1994, 45, 159-646. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995.
3. For excellent reviews, see: (a) Hyatt, J.; Raynolds, R. W. Org. React. 1994, 45, 159-646. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995.
4. The Chemistry of Ketenes, Allnes and Related Compounds; Patai, S., Ed.; The Chemistry of Functional Groups; Wiley: Chichester, U.K., 1980; Parts 1 and 2.
5. (a) Ulrich, H. Cycloaddition Reactions of Hetrocumulenes; Academic Press: New York, 1967.
6. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, CA, 1987.
7. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
8. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
9. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
10. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
11. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
12. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
13. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
14. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
15. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
16. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
17. For representative literature, see: (a) Martin, J. C.; Gott, P. G.; Goodlett, V. W.; Hasek, R. H. J. Org. Chem. 1965, 30, 4175-4180. (b) England, D. C.; Krespan, C. G. J. Org. Chem. 1970, 35, 3300-3307. (c) Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1974, 989-990. (d) Gouesnard, J. P. Tetrahedron 1974, 30, 3113-3117. (e) Brady, W. T.; Agho, M. O. Synthesis 1982, 500-502. (f) Brady, W. T.; Agho, M. O. J. Hetrocycl. Chem. 1983, 20, 501-506. (g) Davies, H. G.; Rahman, S. S.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Perkin Trans. 1 1987, 85-89. (h) Mayr, H.; Heigl, W. J. Chem. Soc., Chem. Commun. 1987, 1804-1805. (i) Dawning, W.; Latouche, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613-2615. (j) Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 41, 6583-6586. (k) Merino, I.; Hegedus, L. S. Organometallics 1995, 14, 2522-2531.
18. Some [4 + 2] cycloadducts were reported to be converted to the [2 + 2] adducts on heating (e.g., 130 °C, 2 days). See: Maurya, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Thomas, R. J.; Williams, J. O J. Chem. Soc., Perkin Trans. 1 1992, 1617-1621. Pittol, C. A.; Roberts, S. M.; Sutton, P. W.; Williams, J. O. J. Chem. Soc., Chem. Commun. 1994, 803-804.
19. Some [4 + 2] cycloadducts were reported to be converted to the [2 + 2] adducts on heating (e.g., 130 °C, 2 days). See: Maurya, R.; Pittol, C. A.; Pryce, R. J.; Roberts, S. M.; Thomas, R. J.; Williams, J. O J. Chem. Soc., Perkin Trans. 1 1992, 1617-1621. Pittol, C. A.; Roberts, S. M.; Sutton, P. W.; Williams, J. O. J. Chem. Soc., Chem. Commun. 1994, 803-804.
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35. Recently, [2 + 2] paths between 1b and 2 (not the [2 + 2] one in Scheme 2) have been reported. Salzner, U.; Bachrach, S. M. J. Org. Chem. 1996, 61, 237-242.
36. a] path in Scheme 1 is concerned with the one-sided transfer.
37. The transition state of the [2 + 2] cycloaddition was determined precisely by Wang and Houk. Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 1754-1756.
38. GAUSSIAN 92 was used for calculations. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. GAUSSIAN 92, Revision C; Gaussian, Inc.: Pittsburgh, PA, 1992.
39. This value of the dielectric constant is taken from a recent theoretical study. Lecea, B.; Arrieta, A.; Lopez, X.; Ugalde, J. M.; Cossio, F. P. J. Am. Chem. Soc. 1995, 117, 12314-12321.
40. 13C NMR δ 212.47 (s, C=O), 134.32 (d, C-2), 131.44 (d, C-3), 80.15 (s, C-7), 58.91 (d, C-5), 49.76 (d, C-1), 34.91 (t, C-4).
41. For accurate analyses, we have applied ID NMR resolution-enhanced with the sine-bell wind function as well as various 2D ones.
42. 2 -60 °C) δ 150.23 (s, C-3), 138.06 (d, C-5), 133.34 (d,C-6), 110.71 (s, C-8), 84.81 (d, C-1), 53.20 (t, C-7), 49.22 (d, C-4).