Contrasting behaviour in the photosolvolysis of 1- and 2-hydroxy-9-fluorenols in aqueous solution

Canadian Journal of Chemistry

Volumn 77, Issue 5-6, 1999, Pages 868-874

  Fischer, Maike ^a   Shi, Yijian ^a   Zhao, Bao Ping ^b   Snieckus, Victor ^b,c   Wan, Peter ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

^b UNIVERSITY OF WATERLOO   (Canada)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

9 fluorenyl cation; Antiaromatic; Carbocation; Photosolvolysis; Quinone methide

Indexed keywords

AROMATIC COMPOUND; BENZYL ALCOHOL; CATION; CHROMAN DERIVATIVE; QUINONE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; KINETICS; NEODYMIUM LASER; PH; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033306137     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjc-77-5-6-868     Document Type: Article

References (21)

1. (a) P. Wan and E. Krogh. J. Chem. Soc. Chem. Commun. 1207 (1985);
2. (b) J. Am. Chem. Soc. 114, 4887 (1989);
3. (c) E. Krogh and P. Wan. Can. J. Chem. 68, 1725 (1990);
4. (d) A. Blazek, M. Pungente, E. Krogh, and P. Wan. J. Photochem. Photobiol. A, 64, 315 (1992).
5. (a) S.L. Mecklenburg and E.F. Hilinski. J. Am. Chem. Soc. 111, 5471 (1989);
6. (b) R.A. McClelland, N. Mathivanan, and S. Steenken. J. Am. Chem. Soc. 112, 4857 (1990);
7. (c) R.A. McClelland. Tetrahedron, 52, 6823 (1996);
8. (d) L.J. Johnston, P. Kwong, A. Shelemay, and E. Lee-Ruff. J. Am. Chem. Soc. 115, 1664 (1993);
9. (e) C.S.Q. Lew, B.D. Wagner, M.P. Angelini, E. Lee-Ruff, J. Lusztyk, and L.J. Johnston. J. Am. Chem. Soc. 118, 12066 (1996);
10. (f) C.S.Q. Lew, D.F. Wong, L.J. Johnston, M. Bertone, A.C. Hopkinson, and E. Lee-Ruff. J. Org. Chem. 61, 6805 (1996).
11. H. Jiao, P. von R. Schleyer, Y. Mo, M.A. McAllister, and T.T. Tidwell. J. Am. Chem. Soc. 119, 7075 (1997).
12. (a) L. Diao, C. Yang, and P. Wan. J. Am. Chem. Soc. 117, 5369 (1995);
13. (b) P. Wan, B. Barker, L. Diao, M. Fischer, Y. Shi, and C. Yang. Can. J. Chem. 74, 465 (1996).
14. J.-M. Fu, B.-P. Zhao, M.J. Sharp, and V. Snieckus. J. Org. Chem. 56, 1683 (1991).
15. F.L. Cozens, N. Mathivanan, R.A. McClelland, and S. Steenken. J. Chem. Soc. Perkin Trans. 2, 2083 (1992).
16. (a) H.E. Zimmerman. J. Am. Chem. Soc. 117, 8988 (1995);
17. (b) H.E. Zimmerman and V.R. Sandel. J. Am. Chem. Soc. 85, 915 (1963).
18. (a) L. Horner and D.W. Baston. Justus Lieb. Ann. Chem. 910 (1973);
19. (b) J. Buckingham (Editor). Dictionary of organic compounds. Vol. 3. 5th ed. Chapman and Hall, New York. 1982. p. H-01815;
20. (c) C.J. Pouchert. The Aldrich library of infrared spectra. Aldrich Chemical Co., Inc., Milwaukee. 1970. p. 660D.
21. C.L. Arcus and M.M. Coombs. J. Am. Chem. Soc. 76, 3977 (1954).