Oxygenation of benzyldimethylamine by singlet oxygen. Products and mechanism

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4791-4794

  Baciocchi, Enrico ^a   Del Giacco, Tiziana ^b   Lapi, Andrea ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; BENZYLDIMETHYLAMINE; DEUTERIUM; FORMAMIDE DERIVATIVE; HYDROGEN; ISOTOPE; METHYLAMINE; OXYGEN; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; OXYGENATION; PHOTOCHEMICAL QUENCHING; PHOTOCHEMISTRY; TEMPERATURE;

EID: 11444260174     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047876l     Document Type: Article

References (42)

1. Schweitzer, C.; Schmidt, R. Chem. Rev. 2003, 103, 1685.
2. (a) Smith, W. F., Jr. J. Am. Chem. Soc. 1972, 94, 186.
3. (b) Bellus, D.; Lind, H. Chem. Commun. 1972, 1199.
4. (c) Peters, G.; Rodgers, M. A. J. Biochim. Biophys. Acta 1981, 637, 43.
5. (d) Manring, L. E.; Foote, C. S. J. Phys. Chem. 1982, 86, 1257.
6. (e) Saito, I.; Matsuura, T.; Inoue, K. J. Am. Chem. Soc. 1983, 105, 3200.
7. (f) Haugen, C. M.; Bergmark, W. R.; Whitten, D. G. J. Am. Chem. Soc. 1992, 114, 10293.
8. (g) Darmanyan A. P.; Jenks, W. S.; Jardon, P. J. Phys. Chem. A 1998, 102, 7420.
9. (h) Bernstein, R.; Foote, C. S. J. Phys. Chem. A 1999, 103, 7244.
10. (i) Cocquet, G.; Rool, P.; Ferroud, C. J. Chem. Soc., Perkin Trans. 1 2000, 14, 2277.
11. Sawyer, D. T.; Chiericato, G., Jr.; Angelis, C. T.; Nanni, E. J., Jr.; Tsuchiya, T. Anal. Chem. 1982, 54, 1720.
12. Inoue, K.; Saito, I.; Matsuura, T. Chem. Lett. 1977, 607.
13. (a) Turro, N. J.; Chow, M. F. J. Am. Chem. Soc. 1981, 103, 7218.
14. (b) Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275.
15. (c) Greer, A.; Vassilikogiannakis, G.; Lee, K.-C.; Koffas, T. S.; Nahm, K.; Foote, C. S. J. Org. Chem. 2000, 65, 6876.
16. (d) Ben-Shabat, S.; Itagaki, Y.; Jockusch, S.; Sparrow, J. R.; Turro, N. J.; Nakanishi, K. Angew. Chem., Int. Ed. 2002, 41, 814.
17. (e) Poon, T.; Turro, N. J.; Chapman, J.; Lakshminarasimhan, P.; Lei, X.; Jockusch, S.; Franz, R.; Washington, I.; Adam, W.; Bosio, S. G. Org. Lett. 2003, 5, 4951.
18. 5a
19. Determined by laser flash photolysis experiments (see Supporting Information).
20. -1) is the same as that for 1, within the experimental error.
21. Darwent, J. R.; Douglas, P.; Harriman, A.; Porter, G.; Richoux, M.-C. Coord. Chem. Rev. 1982, 44, 83.
22. With longer reaction times, higher conversions can be reached but significant overoxidation takes place. Thus, after 90 min of irradiation with 5% TPP, the conversion of 1 is 90% complete, but the yield of 3 + 4 is only 50%.
23. Silverman, S. K.; Foote, C. S. J. Am. Chem. Soc. 1991, 113, 7672.
24. Wilkinson, F.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1995, 24, 663.
25. -1 at 20 and -15°C, respectively.
26. (b) Gorman, A. A.; Gould, I. R.; Hamblett, I.; Standen, M. C. J. Am. Chem. Soc. 1984, 106, 6956.
27. Manring, L. E.; Kramer, M. K.; Foote, C. S. Tetrahedron Lett. 1984, 25, 2523.
28. 15b In this study, however, the reaction products were not investigated
29. (b) Saito, I.; Matsuura, T.; Inoue, K. J. Am. Chem. Soc. 1981, 103, 188.
30. (a) Young, R. H.; Martin, R. L.; Feriozi, D.; Brewer, D.; Kayser, R. Photochem. Photobiol. 1973, 17, 233.
31. (b) Clennan, E. L.; Noe, L. J.; Wen, T.; Szneler, E. J. Org. Chem. 1989, 54, 3581.
32. (c) Gorman, A. Adv. Photochem. 1992, 17, 217.
33. (d) Martin, N. H.; Allen, N. W., III; Cottle, C. A.; Marschke, C. K., Jr. J. Photochem. Photobiol. A 1997, 103, 33.
34. Wagner, P.; Park, B.-S Org. Photochem. 1991, 11, 227.
35. inter.
36. Gollnick, K.; Lindner, J. K. E. Tetrahedron Lett. 1973, 21, 1903.
37. 2 was quantitatively determined by titration with iodide ion (see Supporting Information).
38. 21b
39. (b) Dombrowski, G. W.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Org. Chem. 1999, 64, 427.
40. Cohen, S. G.; Stein, N. M. J. Am. Chem. Soc. 1971, 93, 6542.
41. Adam, W.; Moorthy, J. N.; Nau, W. M.; Scaiano, J. C. J. Am. Chem. Soc. 1997, 119, 6749.
42. Hall, L. R.; Iwamoto, R. T.; Hanzlik, R. P. J. Org. Chem. 1989, 54, 2446.