Kinetic solvent effects on hydrogen abstraction reactions

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2899-2902

  Koner, Apurba L ^a   Pischel, Uwe ^b   Nau, Werner M ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

^b UNIVERSITY OF HUELVA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547193702     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071165g     Document Type: Article

References (40)

1. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, Germany, 2003.
2. Das, P. K.; Encinas, M. V.; Steenken, S.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 4162-4166.
3. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-9971.
4. Avila, D. V.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 2929-2930.
5. MacFaul, P. A.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 1316-1321.
6. Valgimigli, L.; Banks, J. T.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1999, 64, 3381-3383.
7. Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477.
8. Nielsen, M. F.; Ingold, K. U. J. Am. Chem. Soc. 2006, 128, 1172-1182.
9. Litwinienko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222-230.
10. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
11. Lucarini, M.; Pedulli, G. F.; Valgimigli, L. J. Org. Chem. 1998, 63, 4497-4499.
12. Valgimigli, L.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 7947-7950.
13. Aliaga, C.; Stuart, D. R.; Aspée, A.; Scaiano, J. C. Org. Lett. 2005, 7, 3665-3668.
14. ..
15. Avila, D. V.; Ingold, K. U.; Di Nardo, A. A.; Zerbetto, F.; Zgierski, M. Z.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 2711-2718.
16. Nau, W. M.; Cozens, F. L.; Scaiano, J. C. J. Am. Chem. Soc. 1996, 118, 2275-2282.
17. Nau, W. M. Ber. Bunsenges. Phys. Chem. 1998, 102, 476-485.
18. Pischel, U.; Nau, W. M. J. Am. Chem. Soc. 2001, 123, 9727-9737.
19. Adam, W.; Moorthy, J. N.; Nau, W. M.; Scaiano, J. C. J. Org. Chem. 1997, 62, 8082-8090.
20. Nau, W. M.; Pischel, U. Photoreactivity of n,π*-Excited Azoalkanes and Ketones. In Organic Photochemistry and Photophysics; Ramamurthy, V., Schanze, K., Eds.; CRC Press: Boca Raton, FL, 2006; Vol. 14, pp 75-129.
21. Nau, W. M.; Greiner, C.; Rau, H.; Olivucci, M.; Robb, M. A. Ber. Bunsenges. Phys. Chem. 1998, 102, 486-492.
22. Sinicropi, A.; Nau, W. M.; Olivucci, M. Photochem. Photobiol. Sci. 2002, 1, 537-546.
23. Sinicropi, A.; Pogni, R.; Basosi, R.; Robb, M. A.; Gramlich, G.; Nau, W. M.; Olivucci, M. Angew. Chem., Int. Ed. 2001, 40, 4185-4189.
24. Nau, W. M.; Greiner, G.; Wall, J.; Rau, H.; Olivucci, M.; Robb, M. A. Angew. Chem., Int. Ed. 1998, 37, 98-101.
25. Nau, W. M.; Adam, W.; Scaiano, J. C. Chem. Phys. Lett. 1996, 253, 92-96.
26. Nau, W. M.; Greiner, G.; Rau, H.; Wall, J.; Olivucci, M.; Scaiano, J. C. J. Phys. Chem. A 1999, 103, 1579-1584.
27. Nau, W. M. J. Am. Chem. Soc. 1998, 120, 12614-12618.
28. Klapstein, D.; Pischel, U.; Nau, W. M. J. Am. Chem. Soc. 2002, 124, 11349-11357.
29. Pischel, U.; Nau, W. M. Photochem. Photobiol. Sci. 2002, 1, 141-147.
30. Lundgren, C. V.; Koner, A. L.; Tinkl, M.; Pischel, U.; Nau, W. M. J. Org. Chem. 2006, 71, 1977-1983.
31. Pischel, U.; Patra, D.; Koner, A. L.; Nau, W. M. Photochem. Photobiol. 2006, 82, 310-317.
32. Das, P. K.; Encinas, M. V.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 4154-4162.
33. The transient absorption-based measurements with cumyloxyl radicals, which required 308 nm excitation, could not be performed in the cases of di- and triphenylmethane; a residual absorbance of these specific samples and an associated strong transient signal interfered. For diphenylmethanol, where the absorbance of the formed ketyl radical prevented also the direct monitoring of cumyloxyl radicals, tert-butoxyl radicals were used instead. They were generated from di-tert-butylperoxide by 308 nm excitation and indirectly followed by observing the rise kinetics of the diphenylhydroxymethyl radical at 335 nm. Cf.: Griller, D.; Howard, J. A.; Marriott, P. R.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 619-623.
34. Hirayama, S. Chem. Phys. Lett. 1981, 79, 114-111.
35. Harmony, M. D.; Talkington, T. L.; Nandi, R. N. J. Mol. Struct. 1984, 125, 125-130.
36. Nau, W. M.; Pischel, U. Angew. Chem., Int. Ed. 1999, 38, 2885-2888.
37. HyperChem 7.01; Hypercube, Inc.: Gainsville, FL, 2002.
38. Zavitsas, A. A.; Pinto, J. A. J. Am. Chem. Soc. 1972, 94, 7390-7396.
39. Zavitsas, A. A.; Chatgilialoglu, C. J. Am. Chem. Soc 1995, 117, 10645-10654.
40. Zavitsas, A. A. J. Am. Chem. Soc. 1998, 120, 6578-6586.