Generation of o-quinone α-carbomethoxymethide by photolysis of methyl 2-hydroxyphenyldiazoacetate in aqueous solution

Physical Chemistry Chemical Physics

Volumn 5, Issue 6, 2003, Pages 1039-1042

  Chiang, Y ^a   Kresge, A J ^a   Zhu, Y ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 QUINONE ALPHA CARBOMETHOXYMETHIDE; 2' ACETOXY 2 HYDROXYPHENYLACETATE; ACETIC ACID; BENZENE DERIVATIVE; BENZYL ALCOHOL METHYL 2 HYDROXYMANDELATE; BUFFER; ISOTOPE; MANDELIC ACID DERIVATIVE; METHYL 2 HYDROXYPHENYLDIAZOACETATE; PERCHLORIC ACID; PHENYLACETIC ACID DERIVATIVE; PHOSPHATE; QUINONE DERIVATIVE; QUINONE METHIDE; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; PHOTOLYSIS; PRECURSOR; ULTRAVIOLET SPECTROSCOPY;

EID: 0037444419     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b211444p     Document Type: Article

References (22)

1. See, e.g. M. Regitz and G. Maas, Diazo Compounds. Properties and Synthesis, Academic Press, New York, 1986, pp. 185-195.
2. Y. Chiang, E. A. Jefferson, A. J. Kresge, V. V. Popik and R.-Q. Xie, J. Phys. Org. Chem., 1998, 11, 610-613.
3. Y. Chiang, A. J. Kresge, N. P. Schepp and R.-Q. Xie, J. Org. Chem., 2000, 65, 1175-1180.
4. (a) P. Wan, B. Barker, L. Diao, M. Fischer, Y. Shi and C. Yang, Can. J. Chem., 1996, 74, 465-475;
5. P. Wan, D. W. Brousmiche, C. Z. Chen, J. Cole, M. Lukeman and M. Xu, Pure Appl. Chem., 2001, 73, 529-534;
6. (b) Y. Chiang, A. J. Kresge and Y. Zhu, J. Am. Chem. Soc., 2001, 123, 8089-8094;
7. (c) Y. Chiang, A. J. Kresge and Y. Zhu, J. Am. Chem. Soc., 2002, 124, 717-722;
8. (d) Y. Chiang, A. J. Kresge and Y. Zhu, J. Am. Chem. Soc., 2002, 124, 6349-6356;
9. (e) Y. Chiang and A. J. Kresge, Photochem. Photobiol. Sci., 2002, 1, 57-70.
10. H. Tomioka and T. Matsushita, Chem. Lett., 1997, 399-400.
11. M. Regitz and G. Maas, Diazo Compounds. Properties and Synthesis, Academic Press, New York, 1986, ch. 9.
12. W. M. Horspool and G. D. Khandelwal, J. Chem. Soc. C, 1971, 3328-3331.
13. R. Howe, B. S. Rao and H. Heyneker, J. Chem. Soc. C, 1967, 2510-2514.
14. A. J. Hoefnagel, J. A. Peters and H. van Bekkum, Recl. Trav. Chim. Pays-Bas., 1996, 115, 353-356.
15. Y. Chiang, M. Hojatti, J. R. Keeffe, A. J. Kresge, N. P. Schepp and J. Wirz, J. Am. Chem. Soc., 1987, 109, 4000-4009.
16. P. Wan and D. Hennig, J. Chem. Soc., Chem. Comm., 1987, 939-941.
17. R. G. Bates, Determination of pH Theory and Practice, Wiley, New York, 1973, pp. 49.
18. (a) A. J. Kresge, R. A. More O'Ferrall and M. F. Powell, in Isotopes in Organic Chemistry, ed. E. Buncel and C. C. Lee, Elsevier, New York, 1987, vol. 7, ch. 4;
19. (b) J. R. Keeffe and A. J. Kresge, in Investigation of Rates and Mechanisms of Reactions, ed., C. F. Bernasconi, Wiley, New York, 1986, pp. 763-764.
20. J. R. Keeffe and A. J. Kresge, in Tile Chemistry of Enols, ed. Z. Rapoport, Wiley, New York, 1990, ch. 7.
21. Y. Chiang, A. J. Kresge, V. V. Popik and N. P. Schepp, J. Am. Chem. Soc., 1997, 119, 10203-10212.
22. T. Okuyama, S. Kawao and T. Fueno, J. Org. Chem., 1981, 46, 4372-4375.