Preparation of diversely substituted triarylmethyl radicals by the quenching of tris(2,3,5,6-tetrathiaaryl)methyl cations with C-, N-, P-, and S-nucleophiles

European Journal of Organic Chemistry

Volumn 2014, Issue 2, 2014, Pages 371-380

  Tormyshev, Victor M ^a,b   Rogozhnikova, Olga Yu ^a   Bowman, Michael K ^c   Trukhin, Dmitry V ^a   Troitskaya, Tatiana I ^a   Vasiliev, Vladimir G ^a   Shundrin, Leonid A ^a   Halpern, Howard J ^d  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^c UNIVERSITY OF ALABAMA   (United States)

^d University of Chicago   (United States)

Author keywords

Carbocations; Electron transfer; Nucleophilic addition; Radicals; Reaction mechanisms

Indexed keywords

EID: 84891873467     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201301161     Document Type: Article

References (41)

1. S. Andersson, F. Radner, A. Rydbeck, R. Servin, L.-G. Wistrand,U. S. Pat. 5530140, 1996 (Chem. Abstr. 1996, 125, 142745v)
2. J. H. Ardenkjaer-Larsen, I. Leunbach, PCT Int. Appl. WO/9709633, 1997 (Chem. Abstr. 1997, 126, 1274245n)
3. S. Andersson, F. Radner, A. Rydbeck, R. Servin, L.-G. Wistrand, U. S. Pat. 5728370, 1998 (Chem. Abstr. 1998, 128, 244054y)
4. M. Thaning, PCT Int. Appl. WO/9839277, 1998 (Chem. Abstr. 1998, 129, 245140f).
5. N. Khan, H. Swartz, Mol. Cell. Biochem. 2002, 234, 341-357.
6. P. Kuppusamy, P. Wang, M. Chzhan, J. L. Zweier, Magn. Reson. Med. 1997, 37, 479-483.
7. Y. Liu, F. A. Villamena, Y. Song, J. Sun, A. Rockenbauer, J. L. Zweier, J. Org. Chem. 2010, 75, 7796-7802.
8. Y. Liu, F. A. Villamena, J. Sun, T. Y. Wang, J. L. Zweier, Free Radical Biol. Med. 2009, 46, 876-883.
9. Y. Liu, F. A. Villamena, J. Sun, Y. Xu, I. Dhimitruka, J. L. Zweier, J. Org. Chem. 2008, 73, 1490-1497.
10. C. Rizzi, A. Samouilov, V. K. Kutala, N. L. Parinandi, J. L. Zweier, P. Kuppusamy, Free Radical Biol. Med. 2003, 35, 1608-1618.
11. B. Driesschaert, V. Marchand, P. Levêque, B. Gallez, J. Marchand-Brynaert, Chem. Commun. 2012, 48, 4049-4051.
12. A. A. Bobko, I. Dhimitruka, D. A. Komarov, V. V. Khramtsov, Anal. Chem. 2012, 84, 6054-6060.
13. I. Dhimitruka, A. A. Bobko, C. M. Hadad, J. L. Zweier, V. V. Khramtsov, J. Am. Chem. Soc. 2008, 130, 10780-10787.
14. Y. Talmon, L. Shtirberg, W. Harneit, O. Yu. Rogozhnikova, V. Tormyshev, A. Blank, Phys. Chem. Chem. Phys. 2010, 12, 5998-6007.
15. M. Elas, D. Hleihel, E. D. Barth, C. R. Haney, K.-H. Ahn, C. A. Pelizzari, B. Epel, M. Kocherginsky, R. R. Weichselbaum, H. J. Halpern, Mol. Imaging Biol. 2011, 13, 1107-1113.
16. R. Halevy, V. Tormyshev, A. Blank, Biophys. J. 2010, 99, 971-978.
17. M. Elas, K.-H. Ahn, A. Parasca, E. D. Barth, D. Lee, C. Haney, H. J. Halpern, Clin. Cancer Res. 2006, 12, 4209-4217.
18. M. Elas, D. D. Williams, A. Parasca, C. Mailer, C. A. Pelizzari, M. A. Lewis, J. N. River, G. S. Karczmar, E. D. Barth, H. J. Halpern, Magn. Reson. Med. 2002, 49, 682-691.
19. J. Leggett, R. Hunter, J. Granwehr, R. Panek, A. J. Perez-Linde, A. J. Horsewill, J. McMaster, G. Smith, W. Köckenberger, Phys. Chem. Chem. Phys. 2010, 12, 5883-5892.
20. J. H. Ardenkjær-Larsen, B. Fridlund, A. Gram, G. Hansson, L. Hansson, M. H. Lerche, R. Servin, M. Thaning, K. Golman, Proc. Natl. Acad. Sci. USA 2003, 100, 10158-10163.
21. Z. Yang, Y. Liu, P. Borbat, J. L. Zweier, J. H. Freed, W. L. Hubbell, J. Am. Chem. Soc. 2012, 134, 9950-9952.
22. Y. Liu, F. A. Villamena, A. Rockenbauer, Y. Song, J. L. Zweier, J. Am. Chem. Soc. 2013, 135, 2350-2356.
23. G. W. Reginsson, N. C. Kunjir, S. Th. Sigurdsson, O. Schiemann, Chem. Eur. J. 2012, 18, 13580-13584.
24. V. M. Tormyshev, A. M. Genaev, G. E. Sal'nikov, O. Yu. Rogozhnikova, T. I. Troitskaya, D. V. Trukhin, V. I. Mamatyuk, D. S. Fadeev, H. J. Halpern, Eur. J. Org. Chem. 2012, 623-629.
25. I. Dhimitruka, M. Velayutham, A. A. Bobko, V. V. Khramtsov, F. A. Villamena, C. M. Hadad, J. L. Zweier, Bioorg. Med. Chem. Lett. 2007, 17, 6801-6805.
26. T. J. Reddy, T. Iwama, H. J. Halpern, V. H. Rawal, J. Org. Chem. 2002, 67, 4635-4639.
27. O. Yu. Rogozhnikova, V. G. Vasiliev, T. I. Troitskaya, D. V. Trukhin, T. V. Mikhalina, H. J. Halpern, V. M. Tormyshev, Eur. J. Org. Chem. 2013, 3447-3455.
28. I. Dhimitruka, A. A. Bobko, T. D. Eubank, D. A. Komarov, V. V. Khramtsov, J. Am. Chem. Soc. 2013, 135, 5904-5910.
29. C. Decroos, T. Prange, D. Mansuy, J. L. Boucher, Y. Li, Chem. Commun. 2011, 47, 4805-4807.
30. C. Decroos, Y. Li, A. Soltani, Y. Frapart, D. Mansuy, J. L. Boucher, Arch. Biochem. Biophys. 2010, 502, 74-80. The latter was generated by the in situ one-electron oxidation of trityl 4b by excess potassium hexachloroiridate(IV) or hydrogen peroxide in the presence of peroxidase enzymes.
31. B. J. Banks, M. J. Calverley, P. J. Edwards, J. Harley-Mason, Tetrahedron Lett. 1981, 22, 1631-1634.
32. S. F. Tayyari, F. Milani-nejad, Spectrochim. Acta, Part A 2000, 56, 2679-2691.
33. J. R. Song, S. I. Lee, J. Ind. Eng. Chem. 1997, 3, 198-202.
34. M. Hagel, J. Liu, O. Muth, H. J. E. Rivera, E. Schwake, L. Sripanom, G. Henkel, G. Dyker, Eur. J. Org. Chem. 2007, 2007, 3573-3582.
35. G. Dyker, M. Hagel, O. Muth, C. Schirrmacher, Eur. J. Org. Chem. 2006, 2006, 2134-2144.
36. S. A. Snyder, T. C. Sherwood, A. G. Ross, Angew. Chem. 2010, 122, 5272-5276;
37. Angew. Chem. Int. Ed. 2010, 49, 5146-5150.
38. Y. Xiao, Z. K. Zhao, P. Liu, J. Am. Chem. Soc. 2008, 130, 2164-2165.
39. L. G. Spears Jr., A. Liao, D. Minsek, E. S. Lewis, J. Org. Chem. 1987, 52, 61-64.
40. M. P. Rančic̈, N. P. Trišovic̈, M. K. Milčic̈, I. A. Ajaj, A. D. Marinkovic̈, J. Mol. Struct. 2013, 1049, 59-68.
41. O. Kajimoto, M. Kobayashi, T. Fueno, Bull. Chem. Soc. Jpn. 1973, 46, 1422-1425.