Efficiency of proton transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of dialkyl acetals of benzaldehyde

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 6, 1997, Pages 1081-1093

  Brown, Christopher J ^a   Kirby, Anthony J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000689285     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700155j     Document Type: Article

References (45)

1. M. L Sinnott, Chem. Rev., 1990, 90, 1171.
2. Q. Wang, R. W. Graham, D. Trimbur, R. A. J. Warren and S. G. Withers, J. Am. Chem. Soc., 1994, 116, 11 595-5.
3. A. J. Kirby, Angew. Chem., Int. Ed. Engl., 1996, 35, 707.
4. S. G. Withers, K. Rupitz, D. Trimbur and R. A. J. Warren, Biochemistry, 1992, 31, 9979.
5. A. J. Kirby and J. M. Percy. J. Chem. Soc., Perkin Trans. 2, 1989, 907.
6. A. J. Kirby and A. Parkinson, J. Chem. Soc., Chem. Commun., 1994, 707.
7. A. J. Kirby, Adv. Phys. Org. Chem., 1980, 17, 183.
8. A. J. Kirby and A. R. Fersht, in Intramolecular Catalysis, eds. E. T. Kaiser and F. J. Kezdy, New York, 1971.
9. B. Capon, M. C. Smith, E. Anderson, R. H. Dahm and G. H. Sankey, J. Chem. Soc., B, 1969, 1038.
10. G.-A. Craze and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1974, 61.
11. A. A. Frost and R. G. Pearson, Kinetics and Mechanism, Wiley, 1961.
12. J. L. Jensen and P. A. Lenz, J. Am. Chem. Soc., 1978, 100, 1291.
13. J. L. Jensen, A. B. Martinez and C. L. Shimazu, J. Org. Chem., 1983, 48, 4175.
14. T. L. Amyes and W. P. Jencks, J. Am. Chem. Soc., 1989, 111, 7888.
15. B. Capon, K. Nimmo and G. L. Reid, J. Chem. Soc., Chem. Commun., 1976, 871.
16. C. J. Brown, Efficient Intramolecular General Acid Catalysis, Thesis, Cambridge, 1995.
17. J. L. Jensen and K. S. Yamaguchi, J. Org. Chem., 1984, 49, 2613.
18. W. P. Jencks and J. Regenstein, in Ionisation Constants, ed. H. A. Sober, Cleveland, Ohio, 1970.
19. A. Awwal and F. Hibbert, J. Chem. Soc., Perkin Trans. 2, 1977, 152.
20. A. J. Kirby and F. O'Carroll, J. Chem. Soc., Perkin Trans. 2, 1994, 649.
21. M. I. Page, personal communication.
22. J. L. Jensen, L. R. Herold, P. A. Lenz, S. Trusty, V. Sergi, K. Bell and P. Rogers, J. Am. Chem. Soc., 1979, 101, 4672.
23. C. J. Brown and A. J. Kirby, Chem. Commun., 1996, 2355.
24. T. H. Fife and T. J. Przystas, J. Am. Chem. Soc., 1979, 101, 1202.
25. R. H. Bromilow and A. J. Kirby, J. Chem. Soc., B, 1972, 149.
26. A. J. Kirby and D. H. Williams, Phil. Trans. Roy. Soc. (London), Ser. A, 1993, 345, 1.
27. S. E. Barber and A. J. Kirby, J. Chem. Soc., Chem. Commun., 1987, 1775.
28. D. D. Perrin and W. F. Armarego, Purification Methods, Pergamon Press, 1988.
29. K. Glasoe and F. A. Long, J. Phys. Chem., 1960, 64, 188.
30. J. Colonge and R. Vuillemet, Bull. Soc. Chim. Fr., 1961, 2235.
31. F. Straus and H. Heinze, Liebigs Ann. Chem., 1932, 292, 191.
32. L. N. Mander and S. P. Sethi, Tetrahedron Lett., 1983, 24, 5425.
33. E. D. Laganis and B. L. Chenard, Tetrahedron Lett., 1984, 25, 5831.
34. P. Beak and B. J. Kokko, J. Org. Chem., 1982, 47, 2822.
35. A. J. Kirby and J. M. Percy, Tetrahedron, 1988, 44, 6919.
36. K.-I. Monta and T. Kobayashi, J. Org. Chem., 1966, 31, 229.
37. Huang-Minlon, J. Am. Chem. Soc., 1946, 68, 2483.
38. M. Harwood and C. Moody, Experimental Organic Chemistry Blackwell, 1989.
39. M. Demuynck, P. D. Clercq and M. Vandewalle, J. Org. Chem., 1979, 44, 4863.
40. R. E. Marriott, Accelerated Cleavage of Phosphate Esters, Thesis, Cambridge, 1994.
41. C. Beckmann, Built-in Polyamine Catalyst for Phosphate Transfer, Thesis, Cambridge, 1997.
42. S. Kim, C. H. Oh, J. S. Ko, K. H. Ahn and V. J. Kim, J. Org. Chem., 1985, 50, 1927.
43. F. C. M Chen and N. L. Benoit, Can. J. Chem., 1976, 54, 3310.
44. R. O. Hutchins and F. J. Dux, J. Org. Chem., 1973, 38, 1961.
45. Prepared by Dr R. M. Schonk of this laboratory.