Radical cation initiated cycloaddition of electron-rich allnes. Evidence for a stepwise mechanism

Acta Chemica Scandinavica

Volumn 51, Issue 2, 1997, Pages 151-157

  Schmittel, Michael ^a   Wöhrle, Clemens ^a   Bohn, Ingo ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001217371     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.51-0151     Document Type: Review

References (39)

1. (a) Gieseler, A., Steckhan, E. and Wiest, O. Synlett (1990) 275;
2. (b) Wiest, O., Steckhan, E. and Grein, F. J. Org. Chem. 57 (1992) 4034; Gürtler, C. F., Blechert, S. and Steckhan, E. Angew. Chem. 107 (1995) 2025; Angew. Chem., Int. Ed. Engl. 34 (1995) 1900.
3. (b) Wiest, O., Steckhan, E. and Grein, F. J. Org. Chem. 57 (1992) 4034; Gürtler, C. F., Blechert, S. and Steckhan, E. Angew. Chem. 107 (1995) 2025; Angew. Chem., Int. Ed. Engl. 34 (1995) 1900.
4. (b) Wiest, O., Steckhan, E. and Grein, F. J. Org. Chem. 57 (1992) 4034; Gürtler, C. F., Blechert, S. and Steckhan, E. Angew. Chem. 107 (1995) 2025; Angew. Chem., Int. Ed. Engl. 34 (1995) 1900.
5. (a) Schmittel, M. and von Seggern, H. Angew. Chem. 103 (1991) 981; Angew. Chem., Int. Ed. Engl. 30 (1991) 999;
6. (a) Schmittel, M. and von Seggern, H. Angew. Chem. 103 (1991) 981; Angew. Chem., Int. Ed. Engl. 30 (1991) 999;
7. (b) Schmittel, M. and von Seggern, H. J. Am. Chem. Soc. 115 (1993) 2165.
8. Bauld, N. L. and Pabon, R. J. Am. Chem. Soc. 105 (1983) 633.
9. (a) Eberson, L. and Olofsson, B. Acta Chem. Scand., Ser. B 42 (1988) 336;
10. (b) Eberson, L. and Olofsson, B. Acta Chem. Scand. 45 (1991) 316.
11. Bauld, N. L. Tetrahedron 45 (1989) 5307.
12. Mlcoch, J. and Steckhan, E. Tetrahedron Lett. 28 (1987) 1081.
13. Recently, there has been a suggestion about the involvement of an electrophile-catalyzed mechanism being operative in the aminium salt initiated Diels-Alder cyclodimerization of cyclohexa-1,3-diene that has been considered, according to most experimental evidence, to constitute a typical radical cation reaction: (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005; (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871; Compelling evidence from several groups and high-level ab initio calculations, however, support a concerted, almost activationless cycloaddition for this substrate at the stage of the radical cation: Jones, C. R., Allman, B. J., Mooring, A. and Spahic, B. J. Am. Chem. Soc. 105 (1983) 652; Calhoun, G. C. and Schuster, G. B. J. Am. Chem. Soc. 106 (1984) 6870; (e) Lorenz, K. T. and Bauld, N. L. J. Am. Chem. Soc. 109 (1987) 1157; (f) Bauld, N. L. J. Am. Chem. Soc. 114 (1992) 5800.
14. Recently, there has been a suggestion about the involvement of an electrophile-catalyzed mechanism being operative in the aminium salt initiated Diels-Alder cyclodimerization of cyclohexa-1,3-diene that has been considered, according to most experimental evidence, to constitute a typical radical cation reaction: (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005; (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871; Compelling evidence from several groups and high-level ab initio calculations, however, support a concerted, almost activationless cycloaddition for this substrate at the stage of the radical cation: Jones, C. R., Allman, B. J., Mooring, A. and Spahic, B. J. Am. Chem. Soc. 105 (1983) 652; Calhoun, G. C. and Schuster, G. B. J. Am. Chem. Soc. 106 (1984) 6870; (e) Lorenz, K. T. and Bauld, N. L. J. Am. Chem. Soc. 109 (1987) 1157; (f) Bauld, N. L. J. Am. Chem. Soc. 114 (1992) 5800.
15. Recently, there has been a suggestion about the involvement of an electrophile-catalyzed mechanism being operative in the aminium salt initiated Diels-Alder cyclodimerization of cyclohexa-1,3-diene that has been considered, according to most experimental evidence, to constitute a typical radical cation reaction: (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005; (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871; Compelling evidence from several groups and high-level ab initio calculations, however, support a concerted, almost activationless cycloaddition for this substrate at the stage of the radical cation: Jones, C. R., Allman, B. J., Mooring, A. and Spahic, B. J. Am. Chem. Soc. 105 (1983) 652; Calhoun, G. C. and Schuster, G. B. J. Am. Chem. Soc. 106 (1984) 6870; (e) Lorenz, K. T. and Bauld, N. L. J. Am. Chem. Soc. 109 (1987) 1157; (f) Bauld, N. L. J. Am. Chem. Soc. 114 (1992) 5800.
16. Recently, there has been a suggestion about the involvement of an electrophile-catalyzed mechanism being operative in the aminium salt initiated Diels-Alder cyclodimerization of cyclohexa-1,3-diene that has been considered, according to most experimental evidence, to constitute a typical radical cation reaction: (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005; (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871; Compelling evidence from several groups and high-level ab initio calculations, however, support a concerted, almost activationless cycloaddition for this substrate at the stage of the radical cation: Jones, C. R., Allman, B. J., Mooring, A. and Spahic, B. J. Am. Chem. Soc. 105 (1983) 652; Calhoun, G. C. and Schuster, G. B. J. Am. Chem. Soc. 106 (1984) 6870; (e) Lorenz, K. T. and Bauld, N. L. J. Am. Chem. Soc. 109 (1987) 1157; (f) Bauld, N. L. J. Am. Chem. Soc. 114 (1992) 5800.
17. Recently, there has been a suggestion about the involvement of an electrophile-catalyzed mechanism being operative in the aminium salt initiated Diels-Alder cyclodimerization of cyclohexa-1,3-diene that has been considered, according to most experimental evidence, to constitute a typical radical cation reaction: (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005; (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871; Compelling evidence from several groups and high-level ab initio calculations, however, support a concerted, almost activationless cycloaddition for this substrate at the stage of the radical cation: Jones, C. R., Allman, B. J., Mooring, A. and Spahic, B. J. Am. Chem. Soc. 105 (1983) 652; Calhoun, G. C. and Schuster, G. B. J. Am. Chem. Soc. 106 (1984) 6870; (e) Lorenz, K. T. and Bauld, N. L. J. Am. Chem. Soc. 109 (1987) 1157; (f) Bauld, N. L. J. Am. Chem. Soc. 114 (1992) 5800.
18. Recently, there has been a suggestion about the involvement of an electrophile-catalyzed mechanism being operative in the aminium salt initiated Diels-Alder cyclodimerization of cyclohexa-1,3-diene that has been considered, according to most experimental evidence, to constitute a typical radical cation reaction: (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005; (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871; Compelling evidence from several groups and high-level ab initio calculations, however, support a concerted, almost activationless cycloaddition for this substrate at the stage of the radical cation: Jones, C. R., Allman, B. J., Mooring, A. and Spahic, B. J. Am. Chem. Soc. 105 (1983) 652; Calhoun, G. C. and Schuster, G. B. J. Am. Chem. Soc. 106 (1984) 6870; (e) Lorenz, K. T. and Bauld, N. L. J. Am. Chem. Soc. 109 (1987) 1157; (f) Bauld, N. L. J. Am. Chem. Soc. 114 (1992) 5800.
19. (a) Bellville, D. J., Wirth, D. D. and Bauld, N. L. J. Am. Chem. Soc. 103 (1981) 718;
20. (b) Bellville, D. J. and Bauld, N. L. J. Am. Chem. Soc. 104 (1982) 2665;
21. (c) Bellville, D. J., Bauld, N. L., Pabon, R. and Gardner, S. A. J. Am. Chem. Soc. 105 (1983) 3584;
22. (d) Pabon, R. A., Bellville, D. J. and Bauld, N. L. J. Am. Chem. Soc. 105 (1983) 5158.
23. Dolbier, W. R., Jr. In: Coxon, J. M., Eds., Advances In Detailed Reaction Mechanisms, Jai Press, Greenwich 1991, Vol. 1, page 127ff.
24. Oxygenation: (a) Gollnick, K. and Schnatterer, A. Tetrahedron Lett. 26 (1985) 173; Electrooxidation in the presence of nucleophiles: (b) Becker, J. Y. and Zinger, B. Tetrahedron 38 (1982) 1677; Becker, J. Y. and Zinger, B. J. Chem. Soc., Perkin Trans. 2 (1982) 395.
25. Oxygenation: (a) Gollnick, K. and Schnatterer, A. Tetrahedron Lett. 26 (1985) 173; Electrooxidation in the presence of nucleophiles: (b) Becker, J. Y. and Zinger, B. Tetrahedron 38 (1982) 1677; Becker, J. Y. and Zinger, B. J. Chem. Soc., Perkin Trans. 2 (1982) 395.
26. Oxygenation: (a) Gollnick, K. and Schnatterer, A. Tetrahedron Lett. 26 (1985) 173; Electrooxidation in the presence of nucleophiles: (b) Becker, J. Y. and Zinger, B. Tetrahedron 38 (1982) 1677; Becker, J. Y. and Zinger, B. J. Chem. Soc., Perkin Trans. 2 (1982) 395.
27. Schlegel, G. and Schäfer, H. J. Chem. Ber. 116 (1983) 960.
28. Klett, M. W. and Johnston, R. P. Tetrahedron Lett. 24 (1983) 1107; Klett, M. W. and Johnston, R. P. J. Am. Chem. Soc. 107 (1985) 6615.
29. Klett, M. W. and Johnston, R. P. Tetrahedron Lett. 24 (1983) 1107; Klett, M. W. and Johnston, R. P. J. Am. Chem. Soc. 107 (1985) 6615.
30. Maruyama, K. and Imahori, H. Chem. Lett. (1988) 725; Maruyama, K. and Imahori, H. J. Org. Chem. 54 (1989) 2692.
31. Maruyama, K. and Imahori, H. Chem. Lett. (1988) 725; Maruyama, K. and Imahori, H. J. Org. Chem. 54 (1989) 2692.
32. Haddaway, K., Somekawa, K., Fleming, P., Tossell, J. A. and Mariano, P. S. J. Org. Chem. 52 (1987) 4239.
33. Schmittel, M. and Wöhrle, C. J. Org. Chem. 60 (1995) 8223.
34. Schmittel, M. and Wöhrle, C. Tetrahedron Lett. 34 (1993) 8434.
35. Schmittel, M., Wöhrle, C. and Bohn, I. Chem. Eur. J. 2 (1996) 1031.
36. pa should not be off from the reversible potentials by more than 260 mV: Nicholson, R. S. and Shain, I. Anal. Chem. 36 (1964) 706.
37. Dunkin, I. R. and Andrews, L. Tetrahedron 41 (1985) 145.
38. Takahashi, O. and Kikuchi, O. Tetrahedron Lett. 32 (1991) 4933.
39. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F. and Stewart, J. J. P. J. Am. Chem. Soc. 107 (1985) 3902.