Mechanism of alkyl phenylglyoxylates photoreaction in the presence of oxygen

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 118, Issue 2, 1998, Pages 75-80

  Hu, Shengkui ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

Laser flash photolysis; Oxygen; Phenylglyoxylates

Indexed keywords

EID: 0006382830     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1010-6030(98)00376-1     Document Type: Article

References (33)

1. S. Hu, Ph.D. Dissertion, Bowling Green State University, 1998.
2. Hu S., Neckers D.C. J. Mater. Chem. 7:1997;1737-1740.
3. Kiwi J., Schnabel W. Macromolecules. 9:1976;468-470.
4. H. Lutz, L. Lindqvist, J. Chem. Soc. Chem. Commun. (1971) 493-494.
5. Pirrung M.C., Tepper R.J. J. Org. Chem. 60:1995;2461-2465.
6. Hu S., Neckers D.C. J. Org. Chem. 61:1996;6407-6415.
7. Hu S., Neckers D.C. J. Org. Chem. 62:1997;755-757.
8. Ford W.E., Rodgers M.A.J. J. Phys. Chem. 98:1994;3822-3831.
9. The aromatic proton signals of the reaction mixture were used as the internal standard. The downfield aromatic signal (~8.0 ppm) is representative of the starting material and its integration was used to indicate the amount of the remaining starting material.
10. Products 2 and 5 were identified by comparing the retention times and mass fraction patterns with authentic samples in GC/MS analyses.
11. 2, a positive pressure was observed due to the CO produced.
12. Small R.D. Jr., Scaiano J.C. J. Am. Chem. Soc. 100:1978;4512-4519.
13. Hu S., Neckers D.C. J. Org. Chem. 62:1997;7827-7831.
14. -1.
15. Morlino E.A., Bohorquez M.D., Neckers D.C., Rodgers M.A.J. J. Am. Chem. Soc. 113:1991;3599-3601.
16. For similar reactions, see references 17-22.
17. Bacha J.D., Kochi J.K. J. Org. Chem. 37:1972;1999.
18. Greene F.D., Savitz M.L., Osterholtz F.D., Lau H.H., Smith W.N., Zanet P.M. J. Org. Chem. 28:1963;55-64.
19. Kochi J.K. J. Am. Chem. Soc. 84:1962;1193-1197.
20. T. Nakamura, Y. Watanabe, H. Tezuka, W.K. Busfield, I.D. Jenkins, E. Rizzardo, S.H. Thang, S. Suyama, Chem. Lett. (1997) 1093-1094.
21. Nakamura T., Busfield W.K., Jenkins I.D., Rizzardo E., Thang S.H., Suyama S. J. Am. Chem. Soc. 119:1997;10987-10991.
22. Walling C.U., Padwa A. J. Am. Chem. Soc. 85:1963;1593-1597.
23. J.B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, London, 1970, pp. 500.
24. 2 does not affect the Norrish type II reaction.
25. Beck G., Kiwi J., Lindenau D., Schnabel W. Eur. Polym. J. 10:1974;1069.
26. Beck G., Dobrowolski G., Kiwi J., Schnabel W. Macromolecules. 8:1975;9-11.
27. Golemba F.J., Guillet J.E. Macromolecules. 5:1972;212-216.
28. Lukác I., Hrdlovic P., Manásck Z., Bellus D. J. Polym. Sci. Part A 1. 9:1971;69-80.
29. Lukác I., Pilka J., Kulicková M., Hrdlovic P. J. Polym. Sci., Polym. Chem. Ed. 15:1977;1645-1653.
30. Davidson R.S., Goodwin D., Fornier de Voilet P. Chem. Phys. Lett. 78:1981;471-474.
31. Davidson R.S., Goodwin D. J. Chem. Soc., Perkin Trans. 2:1982;1559-1564.
32. Davidson R.S., Goodwin D., Pratt J.E. Tetrahedron. 39:1983;1069-1074.
33. R.S. Davidson, D. Goodwin, J.E. Pratt, J. Chem. Soc, Perkin Trans. II (1983) 1559-1564.