Regio- and diastereoselective rearrangement of cyclopentane-1,3-diyl radical cations generated by electron transfer

Chemical Society Reviews

Volumn 28, Issue 6, 1999, Pages 359-365

  Adam, Waldemar ^a,b   Heidenfelder, Thomas ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033448451     PISSN: 03060012     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903931g     Document Type: Article

References (37)

1. For a recent review, see: M. Schmittel and A. Burghart, Angew. Chem., Int. Ed. Engl., 1997, 36, 2551.
2. W. Adam, V.-I. Handmann, F. Kita and T. Heidenfelder, J. Am. Chem. Soc., 1998, 120, 831.
3. W. Adam and T. Heidenfelder, J. Am. Chem. Soc., 1998, 120, 11858.
4. W. Adam, A. Corma, M. A. Miranda, M.-J. Sabater-Picot and C. Sahin, J. Am. Chem. Soc., 1996, 118, 2380.
5. W. Adam and C. Sahin, Tetrahedron Lett., 1994, 35, 9027.
6. W. Adam and T. Kammel, J. Org. Chem., 1996, 61, 3172.
7. W. Adam, T. Heidenfelder and C. Sahin, J. Am. Chem. Soc., 1995, 117, 9693.
8. W. Adam and J. Sendelbach, J. Org. Chem., 1993, 58, 5310.
9. G. Boche and H. M. Walborsky, in Updates from the Chemistry of Functional Groups: Cyclopropane-derived Reactive Intermediates, ed. S. Patai and Z. Rappaport, John Wiley and Sons, Chichester, 1990, ch. 5, pp. 207-236.
10. H. D. Roth, Top. Curr. Chem., 1992, 163, 131.
11. T. Herbertz and H. D. Roth, J. Am. Chem. Soc., 1998, 120, 11904.
12. J. P. Dinnocenzo and D. A. Conlon, J. Am. Chem. Soc., 1988, 110, 2324.
13. P. G. Gassmann and B. A. Hay, J. Am. Chem. Soc., 1985, 107, 4075.
14. T. Miyashi, Y. Takahashi, H. Ohaku, H. Ikeda and S.-I. Morishima, Pure Appl. Chem., 1991, 63, 223.
15. S. Nishida, M. Murakami, H. Oda, T. Tsuji, T. Mizuno, M. Matsubara and N. Kikai, J. Org. Chem., 1989, 54, 3859.
16. J. P. Dinnocenzo, T. R. Simpson, H. Zuilhof, W. P. Todd and T. Heinrich, J. Am. Chem. Soc., 1997, 119, 987.
17. P. Du, D. A. Hrovat and W. T. Borden, J. Am. Chem. Soc., 1988, 110, 3405.
18. N. G. Connelly and W. E. Geiger, Chem. Rev., 1996, 96, 877.
19. G. J. Kavarnos, Fundamentals of Photoinduced Electron Transfer, VCH, New York, 1993.
20. G. J. Kavarnos, Top. Curr. Chem., 1990, 156, 21.
21. W. Schmidt and E. Steckhan, Chem. Ber., 1980, 113, 577.
22. L. Eberson and B. Olofsson, Acta Chem. Scand., 1991, 45, 316.
23. W. Adam, H. Walter, G.-F. Chen and F. Williams, J. Am. Chem. Soc., 1992, 114, 3007.
24. W. Adam, C. Sahin, J. Sendelbach, H. Walter, G.-F. Chen and F. Williams, J. Am. Chem. Soc., 1994, 116, 2576.
25. W. Adam, T. Kammel and S. Steenken, Angew. Chem., Int. Ed. Engl., 1996, 35, 543.
26. W. Adam, T. Kammel, M. Toubartz and S. Steenken, J. Am. Chem. Soc., 1997, 119, 10673.
27. W. Adam and J. Sendelbach, J. Org. Chem., 1993, 58, 5316.
28. W. Adam and M. Dörr, J. Am. Chem. Soc., 1987, 109, 1570.
29. W. Adam and S. E. Bottle, Tetrahedron Lett., 1991, 32, 1405.
30. W. Adam, S. E. Bottle, R. Finzel, T. Kammel, E.-M. Peters, K. Peters, H. G. von Schnering and L. Walz, J. Org. Chem., 1992, 57, 982.
31. P. J. Kropp, in Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York, 1979, vol. 4, pp. 1-142.
32. S. Dai, J. T. Wang and F. Williams, J. Chem. Soc., Perkin Trans, 1, 1989, 1063.
33. W. Adam, U. Denninger, R. Finzel, F. Kita, H. Platsch, H. Walter and G. Zang, J. Am. Chem. Soc., 1992, 114, 5027.
34. W. Adam, L. Blancafort and M. A. Robb, J. Am. Chem. Soc., in press.
35. J. W. Wilz, in Free Radicals, ed. J. K. Kochi, John Wiley and Sons, New York, 1973, vol. I, ch. 8, pp. 333-501.
36. A. L. J. Beckwith and K. U. Ingold, in Rearrangements in Ground and Excited States, Academic Press, New York, 1980, vol. 1, ch. 4, pp. 161-310.
37. W. Adam, T. Heidenfelder and C. Sahin, Synthesis, 1995, 1163.