Alkoxide-catalysed hydrolyses of a chlorotriazine in alcohol-water mixtures. A new indirect probe for hydroxide-catalysed hydrolysis

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 11, 2000, Pages 2171-2176

  Bentley, T William ^a   Morris, Paul J ^a   Taylor, John A ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYST ACTIVITY; DYES; METHANOL; MIXTURES; PH EFFECTS; PROBES; RATE CONSTANTS; SALTS; SODIUM COMPOUNDS;

ALCOHOLYSES; ALKOXIDE-CATALYSED HYDROLYSIS; DICHLOROTRIAZINE DYES; HYDROXIDE-CATALYSED HYDROLYSIS; MONOFLUOROTRIAZINE; POLYOLS; PROPANOL; SODIUM CARBONATE; SOLVOLYSIS; TETRAALKYLAMMONIUM SALTS;

HYDROLYSIS;

EID: 0034334739     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005949h     Document Type: Article

References (42)

1. (a) M. H. Fernandez and R. H. de Rossi, J. Org. Chem., 1999, 64, 6000
2. (b) W. P. Jencks and J. Carriuolo, J. Am. Chem. Soc., 1961, 83, 1743.
3. (a) E. K. Euranto and N. J. Cleve, Acta Chem. Scand., 1963, 17, 1584
4. (b) D. Stefanidis and W. P. Jencks, J. Am. Chem. Soc., 1993, 115, 6045.
5. A. R. Butler and V. Gold, J. Chem. Soc., 1961, 2305.
6. W. Blokzijl, J. B. N. Engberts and M. J. Blandamer, J. Am. Chem. Soc., 1986, 108, 6411.
7. (a) T. W. Bentley and H. C. Harris, J. Org. Chem., 1988, 53, 724
8. (b) B. D. Song and W. P. Jencks, J. Am. Chem. Soc., 1989, 111, 8470
9. (c) I. S. Koo, I. Lee, J. Oh, K. Yang and T. W. Bentley, J. Phys. Org. Chem., 1993, 6, 223.
10. T. W. Bentley and R. O. Jones, J. Chem. Soc., Perkin Trans. 2, 1993, 2351.
11. (a) R. H. de Rossi and A. Veglia, Int. J. Chem. Kinet., 1985, 17, 859
12. (b) R. H. de Rossi and A. Veglia, J. Org. Chem., 1983, 48, 1879
13. (c) F. Terrier, F. Millot and W. P. Norris, J. Am. Chem. Soc., 1976, 98, 5883
14. (d) R. P. Kelly, R. A. More O'Ferrall and M. O'Brien, J. Chem. Soc., Perkin Trans. 2, 1982, 211
15. (e) I. M. Kovach, A. J. Bennet, J. A. Bibbs and Q. Zhao, J. Am. Chem. Soc., 1993, 115, 5138.
16. A. J. Kirby, in Comprehensive Chemical Kinetics, ed. C. H. Bamford and C. F. H. Tipper, Elsevier, Amsterdam, 1972, Vol. 10, p. 162
17. W. P. Jencks, J. Am. Chem. Soc., 1972, 94, 4731.
18. J. Murto, in The Chemistry of the Hydroxyl Group, Part 2, ed. S. Patai, Interscience, New York, 1971, ch. 20.
19. (a) T. W. Bentley, J. Ratcliff, A. H. M. Renfrew and J. A. Taylor, J. Chem. Soc., Perkin Trans. 2, 1996, 2377
20. (b) T. W. Bentley, J. Ratcliff, A. H. M. Renfrew and J. A. Taylor, J. Soc. Dyers Colour., 1995, 111, 288.
21. S. J. Plust, J. R. Loehe, F. J. Feher, J. H. Benedict and H. F. Herbrandson, J. Org. Chem., 1981, 46, 3661.
22. R. Gary, R. G. Bates and R. A. Robinson, J. Phys. Chem., 1964, 68, 3806.
23. (a) J. Murto, Acta Chem. Scand., 1964, 18, 1029
24. (b) J. Murto, Acta Chem. Scand., 1964, 18, 1043.
25. A. J. Kresge, Chem. Soc. Rev., 1973, 4, 475.
26. (a) L. Michaelis, Ber., 1913, 246, 3683
27. (b) R. N. Totty, PhD Thesis, University of Edinburgh, 1968.
28. P. Ballinger and F. A. Long, J. Am. Chem. Soc., 1960, 82, 795.
29. L. P. Hammett, Physical Organic Chemistry, McGraw Hill, New York, 2nd edn., 1970, p. 319.
30. A. H. M. Renfrew, J. A. Taylor, J. M. J. Whitmore and A. Williams, J. Chem. Soc., Perkin Trans. 2, 1994, 2389.
31. M. Henchman, J. F. Paulson and P. M Hier, J. Am. Chem. Soc., 1983, 105, 5509.
32. E. Tommila and M.-L. Murto, Acta Chem. Scand., 1963, 17, 1947.
33. C. D. Ritchie, J. Am. Chem. Soc., 1975, 97, 1170.
34. C. D. Hall and C. W. Goulding, J. Chem. Soc., Perkin Trans. 2, 1994, 1471.
35. (a) J. P. Guthrie, J. Am. Chem. Soc., 1991, 113, 3941
36. (b) J. P. Guthrie, J. Am. Chem. Soc., 1996, 118, 12886
37. J. P. Guthrie and V. Pitchko, J. Am. Chem. Soc., 2000, 122, 5520.
38. C. A. Bunton and L. Robinson, J. Am. Chem. Soc., 1968, 90, 5965.
39. C. M. Starks, C. L. Liotta and M. Halpern, Phase Transfer Catalysis, Fundamentals, Applications and Industrial Perspectives, Chapman and Hall, New York, 1994, p. 182.
40. W. J. Mulder and J. B. F. N. Engberts, J. Org. Chem., 1988, 53, 3353.
41. (a) T. J. Broxton and D. B. Sango, Aust. J. Chem., 1983, 36, 711
42. (b) C. A. Bunton and L. Robinson, J. Am. Chem. Soc., 1968, 90, 5972.