One-electron oxidation of enol phosphates, enol phosphites and enol phosphinates. Evidence for an unprecedented P-O bond cleavage in phosphoenol radical cations in solution

Chemical Communications

Volumn , Issue 20, 1996, Pages 2349-2350

  Schmittel, Michael ^a   Steffen, Jens Peter ^a   Burghart, Armin ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003696040     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002349     Document Type: Article

References (27)

1. For Part 10 in the series, Enol Radical Cations in Solution, see M. Schmittel and A. Langels, Angew. Chem., Int. Ed. Engl., submitted.
2. M. Chanon, M. Rajzmann and F. Chanon, Tetrahedron, 1990, 46, 6193; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer Verlag, Berlin, 1987.
3. M. Chanon, M. Rajzmann and F. Chanon, Tetrahedron, 1990, 46, 6193; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer Verlag, Berlin, 1987.
4. N. L. Bauld, Adv. Electron Transfer Chem., 1992, 2, 1; N. L. Bauld, Tetrahedron, 1989, 45, 5307; A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 1991, 56, 1405; M. Schmittel and H. von Seggern, Angew. Chem., Int. Ed. Engl., 1991, 30, 999; M. Schmittel and H. von Seggern, J. Am. Chem. Soc., 1993, 115, 2165; M. Schmittel and C. Wöhrle, Tetrahedron Lett., 1993, 34, 8431.
5. N. L. Bauld, Adv. Electron Transfer Chem., 1992, 2, 1; N. L. Bauld, Tetrahedron, 1989, 45, 5307; A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 1991, 56, 1405; M. Schmittel and H. von Seggern, Angew. Chem., Int. Ed. Engl., 1991, 30, 999; M. Schmittel and H. von Seggern, J. Am. Chem. Soc., 1993, 115, 2165; M. Schmittel and C. Wöhrle, Tetrahedron Lett., 1993, 34, 8431.
6. N. L. Bauld, Adv. Electron Transfer Chem., 1992, 2, 1; N. L. Bauld, Tetrahedron, 1989, 45, 5307; A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 1991, 56, 1405; M. Schmittel and H. von Seggern, Angew. Chem., Int. Ed. Engl., 1991, 30, 999; M. Schmittel and H. von Seggern, J. Am. Chem. Soc., 1993, 115, 2165; M. Schmittel and C. Wöhrle, Tetrahedron Lett., 1993, 34, 8431.
7. N. L. Bauld, Adv. Electron Transfer Chem., 1992, 2, 1; N. L. Bauld, Tetrahedron, 1989, 45, 5307; A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 1991, 56, 1405; M. Schmittel and H. von Seggern, Angew. Chem., Int. Ed. Engl., 1991, 30, 999; M. Schmittel and H. von Seggern, J. Am. Chem. Soc., 1993, 115, 2165; M. Schmittel and C. Wöhrle, Tetrahedron Lett., 1993, 34, 8431.
8. N. L. Bauld, Adv. Electron Transfer Chem., 1992, 2, 1; N. L. Bauld, Tetrahedron, 1989, 45, 5307; A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 1991, 56, 1405; M. Schmittel and H. von Seggern, Angew. Chem., Int. Ed. Engl., 1991, 30, 999; M. Schmittel and H. von Seggern, J. Am. Chem. Soc., 1993, 115, 2165; M. Schmittel and C. Wöhrle, Tetrahedron Lett., 1993, 34, 8431.
9. N. L. Bauld, Adv. Electron Transfer Chem., 1992, 2, 1; N. L. Bauld, Tetrahedron, 1989, 45, 5307; A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 1991, 56, 1405; M. Schmittel and H. von Seggern, Angew. Chem., Int. Ed. Engl., 1991, 30, 999; M. Schmittel and H. von Seggern, J. Am. Chem. Soc., 1993, 115, 2165; M. Schmittel and C. Wöhrle, Tetrahedron Lett., 1993, 34, 8431.
10. M. Schmittel, Top. Curr. Chem., 1994, 169, 183.
11. M. Schmittel and M. Levis, Chem. Lett., 1994, 1939.
12. B. B. Snider and T. Kwon, J. Org. Chem., 1992, 57, 2399; B. B. Snider and T. Kwon, J. Org. Chem., 1990, 55, 4786; A. Heidbreder and J. Mattay, Tetrahedron Lett., 1992, 33, 1973.
13. B. B. Snider and T. Kwon, J. Org. Chem., 1992, 57, 2399; B. B. Snider and T. Kwon, J. Org. Chem., 1990, 55, 4786; A. Heidbreder and J. Mattay, Tetrahedron Lett., 1992, 33, 1973.
14. B. B. Snider and T. Kwon, J. Org. Chem., 1992, 57, 2399; B. B. Snider and T. Kwon, J. Org. Chem., 1990, 55, 4786; A. Heidbreder and J. Mattay, Tetrahedron Lett., 1992, 33, 1973.
15. E. Baciocchi, A. Casu and R. Ruzziconi, Tetrahedron Lett., 1989, 30, 3707.
16. P. G. Gassman and J. Bottorff, J. Org. Chem., 1988, 53, 1097.
17. S. S. Mao, T. P. Holler, G. X. Yu, J. M. Bollinger, S. Booker, M. I. Johnston and J. A. Stubbe, Biochemistry, 1992, 31, 9733.
18. P. Maslak and J. N. Narvaez, Angew. Chem., Int. Ed. Engl., 1990, 29, 283.
19. M. Schmittel, G. Gescheidt and M. Röck, Angew. Chem., Int. Ed. Engl., 1994, 33, 1961.
20. M. Schmittel, J. Heinze and H. Trenkle, J. Org. Chem., 1995, 60, 2726.
21. M. Schmittel, M. Keller and A. Burghart, J. Chem. Soc., Perkin Trans. 2, 1995, 2327.
22. H. Hart, Z. Rappoport and S. E. Biali, The Chemistry of Enols, ed. Z. Rappoport, Wiley, New York, 1990, p. 481.
23. R. S. Nicholson and I. Shain, Anal. Chem., 1964, 36, 706.
24. M. Röck and M. Schmittel, J. Chem. Soc., Chem. Commun., 1993, 1739.
25. M. Schmittel and U. Baumann, Angew. Chem., Int. Ed. Engl., 1990, 29, 541; M. Röck and M. Schmittel, J. Prakt. Chem., 1994, 336, 325.
26. M. Schmittel and U. Baumann, Angew. Chem., Int. Ed. Engl., 1990, 29, 541; M. Röck and M. Schmittel, J. Prakt. Chem., 1994, 336, 325.
27. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.