gem-Dialkyl Effect in the Intramolecular Diels-Alder Reaction of 2-Furfuryl Methyl Fumarates: The Reactive Rotamer Effect, Enthalpie Basis for Acceleration, and Evidence for a Polar Transition State

Journal of the American Chemical Society

Volumn 113, Issue 1, 1991, Pages 224-232

  Jung, Michael E ^a   Gervay, Jacquelyn ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001609007     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00001a032     Document Type: Article

References (48)

1. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum: New York, 1976; Vol. 1, pp 43–75.
2. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
3. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080.
4. Ingold, C. K. J. Chem. Soc. 1921, 119, 305.
5. Schleyer, P. V. R. J. Am. Chem. Soc. 1961, 83, 1368.
6. Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858.
7. Jung, M. E. Synlett 1990, 186.
8. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
9. Jung, M. E.; Gervay, J. Tetrahydron Lett. 1988, 29, 2429.
10. Guggenheim, E. A. Philos. Mag. 1926, 2, 538.
11. Kezdy, F. J.; Jaz, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1958, 67, 687.
12. Swinbourne, E. S. J. Chem. Soc. 1960, 2371.
13. Moore, P. J. Chem. Soc, Faraday Trans. 1 1972, 68, 1890.
14. Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions; Wiley: New York, 1963; pp 324–342.
15. Linert, W.; Jameson, R. F. Chem. Soc. Rev. 1989, 18, 477.
16. Cauwberghs, S.; De Clercq, P. J.; Tinant, B.; Declercq, J. P. Tetrahedron Lett. 1988, 29, 2493.
17. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701.
18. Hill, E. A.; Link, D. C.; Donndelinger, P. J. Org. Chem. 1981, 46, 1177.
19. Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum: New York, 1976; Vol. 1, pp 43–75.
20. Boeckman, R. K.; Jr.; Ko, S. S. J. Am. Chem. Soc. 1982, 104, 1033.
21. Taylor, E. C.; Pont, J. L. J. Org. Chem. 1987, 52, 4287.
22. Eberson, L.; Welinder, H. J. Am. Chem. Soc. 1971, 93, 5821.
23. Harfenist, M.; Thom, E. J. Org. Chem. 1972, 37, 841.
24. Jager, J.; Graafland, T.; Schenk, H.; Kirby, A. J.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1984, 106, 139.
25. DeTar, D. F.; Luthra, N. P. J. Am. Chem. Soc. 1980, 102, 4505.
26. Gschwend, H. W.; Lee, A. O.; Meier, H.-P. J. Org. Chem. 1973, 38, 2169.
27. Okamura, W. H.; Curtin, M. L. Synlett 1990, 1.
28. Sternbach, D. D.; Rossana, D. M.; Onan, K. D. Tetrahedron Lett. 1985, 26, 591.
29. Galli, C.; Giovannelli, G.; Illuminati, G.; Mandolini, L. J. Org. Chem. 1979, 44, 1258.
30. Brown, R. F.; van Gulick, N. M. J. Org. Chem. 1956, 21, 1046.
31. Milstien, S.; Cohen, L. A. Proc. Natl. Acad. Sci. U.S.A. 1970, 67, 1143
32. J. Am. Chem. Soc. 1972, 94, 9158.
33. Borchardt, R. T.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 9166, 9175.
34. Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
35. Wassermann, A. Diels-Alder Reactions; Elsevier: Amsterdam, 1965.
36. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988.
37. Reichardt, C. Angew. Chem., Int. Ed. Engl. 1965, 4, 29.
38. Berson, J. A.; Hamlet, Z.; Mueller, W. A. J. Am. Chem. Soc. 1962, 84, 297.
39. Dale, J. Stereochemistry and Conformational Analysis; Verlag Chemie: New York, 1978; pp 83–85.
40. Testa, B. Principles of Organic Stereochemistry; Marcel Dekker: New York, 1979; p 105.
41. Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. Conformational Analysis; Interscience: New York, 1965; p 21.
42. Jung, M. E.; Gervay, J. Tetrahedron Lett. 1990, 31, 4685.
43. Dunlop, A. P.; Peters, F. N. The Furans; Reinhold Publishing: New York, 1953; pp 254–258.
44. Spatz, S. M.; Stone, H. J. Org. Chem. 1958, 23, 1559.
45. Eisner, U.; Elvidge, J. A.; Linstead, R. P. J. Chem. Soc. 1951, 1501.
46. Ivanov, A. A.; Primelles, E.; Delgado, R. CENTRO, Ser.: Quim. Tecnol. Quirn. 1975, 3, 19
47. Chem. Abstr. 1977, 86, 5239v.
48. Murahashi, S.-I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002.