Volume of concert and heavy atom effects in Diels-Alder reaction mechanisms

Tetrahedron

Volumn 52, Issue 46, 1996, Pages 14459-14468

  Firestone, Raymond A ^a,b  

^a BRISTOL MYERS SQUIBB   (United States)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; CYCLOHEXENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ISOTOPE LABELING; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 0030580424     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00891-5     Document Type: Article

References (46)

1. 1. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry. Academic Press, N. Y., 1970.
2. 2. Doering, W. E.; Sachdev, K. J. Am. Chem. Soc. 1975, 97, 5512-5520.
3. 4, but the absence of these and of significant solvent effects in the cases herein discussed allows us to consider diradical and concerted pathways only.
4. 4. Lücking, K.; Rese, M.; Sustmann, R. Liebig's Ann. 1995, 1129-1138; Rese, M.; Dern, M.; Lücking, K.; Sustmann, R. ibid., 1139-1162.
5. 4. Lücking, K.; Rese, M.; Sustmann, R. Liebig's Ann. 1995, 1129-1138; Rese, M.; Dern, M.; Lücking, K.; Sustmann, R. ibid., 1139-1162.
6. 5. Benford, G. A.; Wasserman, A. J. Chem. Soc. 1939, 362; Wasserman, A. J. Chem. Soc. 1942, 612.
7. 5. Benford, G. A.; Wasserman, A. J. Chem. Soc. 1939, 362; Wasserman, A. J. Chem. Soc. 1942, 612.
8. 6. Stewart, C. A., Jr. J. Am. Chem. Soc. 1972, 94, 635-637.
9. 7. Billingham, N. C.; Ebdon, J. R.; Lehrle, R. S.; Markham, J. L.; Robb, J. C. Trans. Far. Soc. 1969, 65, 470-488.
10. 8. Stewart, C. A., Jr. J. Am. Chem. Soc. 1971, 93, 4815.
11. 9. Klärner, F-G.; Krawczyk, B.; Ruster, V.; Deiters, U. K. J. Am. Chem. Soc. 1994, 116, 7646-7657.
12. 10. Little, J. C. J. Am. Chem. Soc. 1965, 87, 4020-4022. In cyclohexane, acetonitrile and nitromethane, variability was small and irregular over 63, 48 and 63-degree ranges respectively, indicating zero energy of concert. In toluene, however, Klärner has found that there is a trend toward more [2 + 2] as the temperature is raised over a 95 degree range, and in this solvent there is an energy of concert of 5.6 Kcal/mol (unpublished results from V. Ruster's Ph. D. thesis, Ruhr-Univ. Bochum, 1987), and an entropy of concert of 9.7 e.u. Note, however, that in the first three solvents the entropy of concert is negative, since [2 + 4] is favored. I thank Dr. Klärner for this information.
13. 11. Firestone, R. A. Tetrahedron 1977, 33, 3009-3039.
14. 12. Firestone, R. A. Heterocycles 1987, 25, 61-64.
15. 13. Griller, D.; Ingold, K.U. Accts. Chem. Res. 1980, 13, 193-200.
16. 14. Hefter, H.J.; Wu, C-H. S.; Hammond, G.S. J. Am. Chem. Soc. 1973, 95, 851-855.
17. 15. Korth, H-G.; Trill, H.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483-4489.
18. 16. Korth, H-G.; Lommes, P.; Sicking, W.; Sustmann, R. Int. J. Chem. Kin. 1983, 15, 267-279.
19. 17. Krusic, P. J.; Meakin, P.; Jesson, J. P. J. Phys. Chem. 1971, 75, 3438-3453.
20. 18. Berson, J. A.; Tompkins, D. C.; Jones III, G. J. Am. Chem. Soc. 1970, 92, 5799.
21. 19. Bartlett, P. D.; Porter, N. A. J. Am. Chem. Soc. 1968, 90, 5317.
22. 20. Dervan, P. B.; Uyehara, T. J. Am. Chem. Soc. 1979, 101, 2076-2080.
23. 21. Butane-1,4-diyl lies in a potential well of 4 Kcal/mol; Pedersen, S.; Herek, J. L.; Zewail, A.H. Science 1994, 266, 1359-1364.
24. 22. Gassman, P. G.; Mansfield, K. T.; Murphy, T. J. J. A.m. Chem. Soc. 1968, 90, 4746.
25. 23. Mark, V. J. Org. Chem. 1974, 39, 3179.
26. 24. Meier, H.; Eckes, H-L.; Niedermann, H-P.; Kolshorn, H. Angew. Chem. Int. Ed. 1987, 26, 1046-1048.
27. 25. McClure, D. S. J. Chem. Phys. 1949, 77, 905.
28. 26. Turro, N.J. Diradicals, Borden, W. T., Ed., Wiley, N.Y. 1982; p. 263.
29. 27. Kasha, M. J. Chem. Phys. 1952, 20, 71-74; Chandra, A.K.; Turro, N.J.; Lyons, A.L., Jr.; Stone, P. J. Am. Chem. Soc. 1978, 100, 4964.
30. 27. Kasha, M. J. Chem. Phys. 1952, 20, 71-74; Chandra, A.K.; Turro, N.J.; Lyons, A.L., Jr.; Stone, P. J. Am. Chem. Soc. 1978, 100, 4964.
31. 28. Koziar, J. C.; Cowan, D. O. Accts. Chem. Res. 1978, 11, 334-341.
32. 29. Lingnau, J.; Meyerhoff, G. Makromol. Chem. 1984, 185, 587-600.
33. 30. Kubo, Y.; Togawa, S.; Yamane, K.; Takuwa, A.; Araki, T. J. Org. Chem. 1989, 54, 4929.
34. 31. Turro, N.J.; Chung, C-J.; Jones II, G.; Becker, W.G. J. Phys. Chem. 1982, 86, 3677.
35. 32. Borecka, B.; Gudmundsdottir, A.D.; Olovsson, G.; Ramamurthy, V.; Scheffer, J.R.; Trotter, J. J. Am. Chem. Soc. 1994, 116, 10322-10323.
36. 33. Fisher, J.J.; Michl, J. J. Am. Chem. Soc. 1987, 109, 583-584.
37. 34. Medinger, T.; Wilkinson, F. Trans. Far. Soc. 1965, 61, 620-630.
38. 35. Horrocks, A.R.; Wilkinson, F. Proc. Roy. Soc. A 1968, 306, 257-273.
39. 36. Bartlett, P.D. Science, 1968, 159, 833-838.
40. 37. Bartlett, P.D.; Dempster, C.J.; Montgomery, L.K.; Schueller, K.E.; Wallbillich, G.E.H. J. Am. Chem. Soc. 1969, 91, 405-409.
41. 38. Bartlett, P.D.; Hull, L. A. J. Org. Chem. 1975, 40, 831-835.
42. 39. Firestone, R. A. J. Org. Chem. 1968, 33, 2285-2290.
43. 40. Durig, J.R.; Church, J.S.; Compton, D.A.C. J. Chem. Phys. 1979, 71, 1175-1182; Compton, D.A.C.; George, W.O.; Goodfield, J.E.; Maddams, W.F. Spectrochim. Acta A 1981, 37A, 147-161.
44. 40. Durig, J.R.; Church, J.S.; Compton, D.A.C. J. Chem. Phys. 1979, 71, 1175-1182; Compton, D.A.C.; George, W.O.; Goodfield, J.E.; Maddams, W.F. Spectrochim. Acta A 1981, 37A, 147-161.
45. 11.
46. 42. Firestone, R.A.; Smith, G.M. Chem. Ber. 1989, 122, 1089-1094, and references therein.