Bimolecular formation of radicals by hydrogen transfer, 12: Transfer hydrogenation of p-substituted α-methylstyrenes and of 9-methylenefluorene as a criterion of mechanism

Liebigs Annales

Volumn , Issue 2, 1997, Pages 385-389

  Friebolin, Heike ^a   Roers, Rolf ^a   Ebenhoch, Jochen ^a   Gerst, Matthias ^a   Rüchardt, Christoph ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Hydrogen atom transfer; Radicals; Retrodisproportionation

Indexed keywords

EID: 14844286572     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970216     Document Type: Article

References (37)

1. H. Friebolin, Dissertation, Univ. Freiburg, in preparation.
2. R. Roers, Diplomarbeit, Univ. Freiburg, 1995.
3. J. Ebenhoch, Dissertation, Univ. Freiburg, 1996.
4. [4a] M. Gerst, Dissertation, Univ. Freiburg, 1994.
5. [4b] For a preliminary publication see M. Gerst, C. Rüchardt, Tetrahedron Lett. 1993, 34, 7733-7736.
6. M. Gerst, C. Rüchardt, Chem. Ber. 1993, 126, 1039-1045.
7. M. Gerst, J. Morgenthaler, C. Rüchardt, Chem. Ber. 1994, 127, 691-696.
8. J. Morgenthaler, C. Rüchardt, Liebigs Ann. 1996, 1529-1532.
9. M. Coellen, C. Ruchardt, Chem. Europ. J. 1995, 1, 564-567.
10. M. Coellen, Dissertation, Univ. Freiburg in preparation.
11. C. Höfler, C. Rüchardt, Liebigs Ann. 1996, 183-188.
12. C. Rüchardt, M. Gerst, M. Nölke, Angew. Chem. 1992, 104, 1516-1518;
13. Angew. Chem. Int. Ed. Engl. 1992, 31, 1523.
14. For a review see: C. Rüchardt, M. Gerst, J. Ebenhoch, Angew. Chem., accepted.
15. L. M. Jackmann, Adv. Org. Chem. 1960, 2, 329-366;
16. J. March, Advanced Organic Chemistry, 4th ed., J. Wiley, New York, 1992, p. 1163.
17. S. W. Benson, Int. J. Chem. Kin. 1980, 12, 755-760.
18. H. Friebolin, C. Ruchardt, Liebigs Ann. 1995, 1339-1341.
19. [1]; cf.: C. Herberg, H.-D. Deckhaus, C. Rüchardt, Chem. Ber. 1994, 127, 2065-2072.
20. D. Seymour, K. B. Wolfstirn, J. Am. Chem. Soc. 1948, 70, 1177-1179.
21. I. L. Knunyants, G. G. Yakobson, Syntheses of Fluoroorganic Compounds, 1st ed., Springer, Berlin-Heidelberg-New York, 1985, p. 126;
22. E. M. Marek, I. P. Kolenko, N. A. Ryabinin, Y. N. Agishev, J. Gen. Chem. USSR 1969, 39, 2257-2260.
23. A. K. Barbour, M. W. Buxton, P. L. Coe, R. Stephens, J. C. Tatlow, J. Chem. Soc. 1961, 808-817.
24. B. S. Nader, J. A. Cordova, K. E. Reese, C. L. Powell, J. Org. Chem. 1994, 59, 2898-2901.
25. F. Ullmann, R. von Wurstemberger, Chem. Ber. 1905, 38, 4105-4110.
26. H. Wieland, E. Krause, Justus Liebigs Ann. Chem. 1925, 443, 129-141;
27. H. H. Schlubach, A. Faltings, Chem. Ber. 1952, 85, 514-520.
28. D. M. Camaioni, S. T. Autrey, T. B. Salinas, J. A. Franz, J. Am. Chem. Soc. 1996, 118, 2013-2022.
29. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH Weinheim, 1988, 409.
30. M. J. Perkins, Radical Chemistry, 1st ed., Ellis Horwood, New York, 1994, p. 27, 42, 114.
31. R. W. Hoffmann, Aufklärung von Reaktionsmechanismen, G. Thieme Verlas, Stutteart, 1976, p. 62.
32. Cf. e.g.: E. M. Arnett, R. A. Flowers, A. E. Meekhof, L. Miller, J. Am. Chem. Soc. 1993, 115, 12603-12604.
33. [28a] B. W. Carlson, L. L. Miller, J. Am. Chem. Soc. 1985, 107, 479-485.
34. [28b] S. Ottoboni, P. Caldera, A. Trevon, N. Castagnoli jr., J. Biol. Chem. 1989, 264, 13684-13688.
35. [28c] N. Brewster, E. Pop, M.-J. Huane, N. Bodor, Heterocycles 1994, 37, 1373-1415.
36. [28d] R. B. Silverman, Acc. Chem. Res. 1995, 28, 335-342.
37. [28e] J. Gebicki, A. Marcinek, J. Adamus, P. Paneth, J. Rocowski, J. Am. Chem. Soc. 1996, 118, 691-692.