Titanium enolate radical cations in solution: generation, characterization, and their reactions

Chemische Berichte

Volumn 130, Issue 6, 1997, Pages 771-777

  Schmittel, Michael ^a   Söllner, Rolf ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Cyclic voltammetry; EPR spectroscopy Radical ion Mesolytic bond cleavage; Titanium enolate

Indexed keywords

EID: 0000436558     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300616     Document Type: Article

References (62)

1. .[21].
2. [2a] M. T. ReetZ; Organotitanium Reagents in Organic Synthesis, Springer-Verlag, Berlin-Heidelberg, 1986.
3. [2b] B. Weidmann, D. Seebach, Angew. Chem. 1983, 95, 12-26; Angew. Chem. Int. Ed. Engl. 1983, 22, 31-45.
4. [3a] J. J A. Dusseault, C. C. Hsu, J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1993, C33, 103-145.
5. [3b] P. C. Mohring, N. J. Coville, J. Organomet. Chem. 1994, 478, 1-29.
6. [3c] J. Huang, G. L. Rempel, Prog. Polym. Sci. 1995, 20, 459-526.
7. [4a] A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582-2609.
8. [4b] J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524.
9. [5a] T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976.
10. [5b] B. E. Rossiter, T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 464-465.
11. [5c] K. B. Sharpless, S. S. Woodard, M. G. Finn, Pure Appl. Chem. 1983, 55, 1823-1836.
12. [6a] A. Choudhury, E. R. Thornton, Tetrahedron 1992, 48, 5701-5708.
13. [6b] D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark, M. T. Bilodeau. J Am. Chem. Soc, 1990, 112, 8215-8216.
14. [6c] S. Shirodkar, M. Nerz-Stormes, E. R. Thornton, Tetrahedron Lett. 1990, 31, 4699-4702.
15. [6d] M. P. Bonner, E. R. Thornton, J. Am. Chem. Soc, 1991, 113, 1299-1308.
16. [6e] D. A. Evans, D. L. Rieger, M. T. Bilodeau, F. Urpi, J. Am. Chem. Soc. 1991, 113, 1047-1049.
17. [6f] R. Mahrwald, Chem. Ber. 1995, 128, 919-921.
18. [6g] A. Solladié-Cavallo, J. L. Koessler, J. Fischer, A. DeCian, Gazz. Chim. Ital. 1996, 126, 173-178.
19. [7a] R. O. Duthaler, P. Herold, W. Lottenbach, K. Oertle, M. Riediker, Angew. Cliem. 1989, 101, 490-491;
20. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-496.
21. [7b] R. O. Duthaler, A. Hafner, Cliem. Rer. 1992, 92, 807-832.
22. D. A. Evans, M. T. Bilodeau, T. C. Somers, J. Clardy, D. Cherry, Y. Kalo, J. Org. Chem. 1991, 56, 5750-5752.
23. [9a] W. Adam, F. Prechtl, Cliem. Ber. 1994, 127, 667-671.
24. [9b] M. Schulz, R. Kluge, M. Schüßler, G. Hoffmann, Tetrahedron 1995, 51, 3175-3180.
25. [9c] W. Adam, M. N. Korb, Tetrahedron 1996, 52, 5487-5494.
26. [10a] A. B. Paolobelli, D. Latini, R. Ruzziconi, Tetrahedron Lett. 1993, 34, 721-724.
27. [10b] B. B. Snider, T. Kwon, J. Org. Chem. 1992, 57, 2399-2410.
28. [10c] A. Heidbreder, J. Mattay, Tetrahedron Lett. 1992, 33, 1973-1976.
29. [10d] H. J. Schäfer in: Organic Electrochemistry, 3rd Ed. (Eds.: H. Lund, M. M. Baizer), Marcel Dekker, New York 1991, 949-1027.
30. [10e] B. B. Snider, T. Kwon, J. Org. Chem. 1990, 55, 4786-4788.
31. [10f] E. Baciocchi, A. Casu, R. Ruzziconi, Tetrahedron Lett. 1989, 30, 3707-3710.
32. Y. Kohno, K. Narasaka, Bull. Cliem. Soc. Jpn. 1995, 68, 322-329.
33. M. Schmittel, R. Söllner, Angew. Cliem. 1996, 108, 2248-2250; Angew. Chem. Int. Ed. Engl. 1996, 35, 2107-2109.
34. [13a] M. D. Curtis, S. Thanedar, W. M. Butler, Organometallics 1984, 3, 1855-1859.
35. [13b] C. P. Gibson, D. S. Bern, J. Organomet. Ciem. 1991, 414, 23-32.
36. [13c] P. Veya, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 4892-4898.
37. [13d] R. Beckhaus, I. Strauß, T. Wagner, J. Organomet. Cliem. 1994, 464, 155-161.
38. [13e] P. Veya, P. G. Cozzi, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1995, 14, 4101-4108.
39. M. Schmittel, H. Werner, O. Gevert, R. Söllner, Chem. Ber. 1997, 130, 195-199.
40. All potentials are referenced to the ferrocene/ferrocenium (Fc) redox couple unless otherwise noted. To obtain values vs. SCE, simply add + 0.39 V.
41. [16a] M. Schmittel, U. Baumann, Angew. Chem. 1990, 102, 571-572; Angew. Chem. Int. Ed. Engl. 1990, 29, 541-543.
42. [16b] M. Schmittel, M. Rock, Chem. Ber. 1992, 125, 1611-1620.
43. M. Schmittel, M. Rock, J. Chem. Soc., Chem. Commun. 1993, 1739-1741.
44. [16d] M. Röck, M. Schmittel, J. Prakt. Chem. 1994, 336, 325-329.
45. R. S. Nicholson, I. Shain, Anal. Chem. 1964, 36, 706-723.
46. [18a] A. Lasia, J. Electroanal. Chem. Interfacial Electrochem. 1983, 146, 397-411.
47. [18b] J. Heinze, M. Störzbach, M. Mortensen, J. Electroanal. Chem. Interfacial Electrochem. 1984, 165, 61-70.
48. [18c] J. Heinze, M. Störzbach, J. Electroanal. Chem. 1993, 346, 1-27.
49. The expression mesolytic was coined by Maslak to describe bond cleavage of radical ions to yield radical and ionic products: P. Maslak, J. N. Narvaez, Angew. Chem. 1990, 102, 302-304;
50. Angew. Chem. Int. Ed. Engl. 1990, 29, 283-285.
51. M. Schmittel, J. Heinze, H. Trenkle, J. Org. Chem. 1995, 60, 2726-2733.
52. M. Schmittel, H. Trenkle, Chem. Lett. 1997, in press.
53. M. Levis, Dissertation, Univ. Freiburg, 1994.
54. M. Schmittel, J.-P. Steffen, A. Burghart, J. Chem. Soc., Chem. Commun. 1996, 2349-2350.
55. S. V. Kukharenko, G. L. Solveichik, V. V. Strelets, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1986, 35, 926-932.
56. M. Schmittel, M. Rock, unpublished results.
57. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
58. [27a] N. P. Schepp, L. J. Johnston, J. Am. Chem. Soc. 1994, 116, 10330-10331.
59. [27b] N. P. Schepp, L. J. Johnston, J. Am. Chem. Soc. 1994, 116, 6895-6903.
60. V. Amamath, D. C. Anthony, K. Amarnath, W. M. Valentine, J. Org. Chem. 1991, 56, 6924-6931.
61. C. Amatore, C. Lefrou and F. Pflügler, J. Electroanal. Chem. Interfacial Electrochem. 1989, 270, 43-59.
62. R. S. Nicholson, Anal. Chem. 1966, 38, 1406.