Flash photolysis of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in aqueous solution: Hydration of acetylketene and ketonization of acetoacetic acid enol

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3386-3391

  Chiang, Y ^a   Guo, H X ^a   Kresge, A J ^a   Tee, O S ^b  

^a UNIVERSITY OF TORONTO   (Canada)

^b Gina Cody School of Engineering and Computer Science   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0029966520     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9540435     Document Type: Article

References (50)

1. For reviews of the early work, see: Ingold, C K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Cornell University Press: Ithaca, NY, 1969, pp 794-837. Wheland, G. W. Advanced Organic Chemistry. 3rd ed.; John Wiley & Sons: New York, 1960; pp 663-703 For a summary of more recent studies, see: Toullec, J. In The Chemistry of Enols; Rappoport, Z , Ed., John Wiley & Sons: New York, 1990; pp 353-378.
2. For reviews of the early work, see: Ingold, C K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Cornell University Press: Ithaca, NY, 1969, pp 794-837. Wheland, G. W. Advanced Organic Chemistry. 3rd ed.; John Wiley & Sons: New York, 1960; pp 663-703 For a summary of more recent studies, see: Toullec, J. In The Chemistry of Enols; Rappoport, Z , Ed., John Wiley & Sons: New York, 1990; pp 353-378.
3. For reviews of the early work, see: Ingold, C K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Cornell University Press: Ithaca, NY, 1969, pp 794-837. Wheland, G. W. Advanced Organic Chemistry. 3rd ed.; John Wiley & Sons: New York, 1960; pp 663-703 For a summary of more recent studies, see: Toullec, J. In The Chemistry of Enols; Rappoport, Z , Ed., John Wiley & Sons: New York, 1990; pp 353-378.
4. (a) Pedersen, K. J. J Phys Chem. 1934, 38, 999-1022
5. (b) Kirby, A. J., Meyer, G. J. Chem. Soc., Perkin Trans. 2 1972, 1446-1451
6. (c) Bell, R. P., Page, M. I. J. Chem. Soc., Perkin Trans. 2 1973, 1681-1686. Cox, B. G.; Hutchinson, R. E. J. J Chem. Soc., Perkin Trans. 2 1974, 613-616.
7. (c) Bell, R. P., Page, M. I. J. Chem. Soc., Perkin Trans. 2 1973, 1681-1686. Cox, B. G.; Hutchinson, R. E. J. J Chem. Soc., Perkin Trans. 2 1974, 613-616.
8. Clemens, R. J.; Witzeman, J. S. J. Am. Chem. Soc. 1989, 111, 2186-2193. Freiermuth, B.; Wentrup, C. J. Org. Chem. 1991, 56, 2286-2289 Kappe, C. O., Wong, M W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695.
9. Clemens, R. J.; Witzeman, J. S. J. Am. Chem. Soc. 1989, 111, 2186-2193. Freiermuth, B.; Wentrup, C. J. Org. Chem. 1991, 56, 2286-2289 Kappe, C. O., Wong, M W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695.
10. Clemens, R. J.; Witzeman, J. S. J. Am. Chem. Soc. 1989, 111, 2186-2193. Freiermuth, B.; Wentrup, C. J. Org. Chem. 1991, 56, 2286-2289 Kappe, C. O., Wong, M W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695.
11. For recent reviews, see. Wentrup, C.; Heilmayer, W.; Kollenz, G Synthesis 1994, 1219-1248. Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995. A recent theoretical study is provided by: Birney, D. M.; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
12. For recent reviews, see. Wentrup, C.; Heilmayer, W.; Kollenz, G Synthesis 1994, 1219-1248. Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995. A recent theoretical study is provided by: Birney, D. M.; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
13. For recent reviews, see. Wentrup, C.; Heilmayer, W.; Kollenz, G Synthesis 1994, 1219-1248. Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995. A recent theoretical study is provided by: Birney, D. M.; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
14. Chiang, Y.; Kresge, A. J ; Schepp, N P. J. Am. Chem. Soc. 1989, 111, 3977-3980.
15. Guthrie, J. P Can. J. Chem. 1993, 71, 2123-2128
16. Hoz, S , Kresge, A. J Unpublished work.
17. (a) Chiang, Y ; Hojatti, M.; Keeffe, J. R ; Kresge, A. J.; Schepp, N.; Wirz, J J. Am. Chem. Soc. 1987, 109, 4000-4009.
18. (b) Andraos, J.; Chiang, Y.; Huang, C.-G.; Kresge, A. J., Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 10605-10610.
19. Supporting information; see paragraph at the end of this paper regarding availablility.
20. (a) Allen, A D.; Kresge, A J., Schepp, N. P.; Tidwell, T T. Can. J. Chem 1987, 65, 1719-1723.
21. (b) Andraos, J.; Kresge, A. J. J Photochem. Photobiol. A 1991, 57, 165-173.
22. Allen, A. D.; Stevenson, A.; Tidwell, T T. J. Org. Chem 1989, 54, 2843-2848. Allen, A. D.; Baigre, L. M.; Gong, L., Tidwell, T. T Can. J. Chem. 1991, 69, 138-145. Andraos, J.; Kresge, A. J.; Schepp, N. P. Can J. Chem 1995, 73, 539-543.
23. Allen, A. D.; Stevenson, A.; Tidwell, T T. J. Org. Chem 1989, 54, 2843-2848. Allen, A. D.; Baigre, L. M.; Gong, L., Tidwell, T. T Can. J. Chem. 1991, 69, 138-145. Andraos, J.; Kresge, A. J.; Schepp, N. P. Can J. Chem 1995, 73, 539-543.
24. Allen, A. D.; Stevenson, A.; Tidwell, T T. J. Org. Chem 1989, 54, 2843-2848. Allen, A. D.; Baigre, L. M.; Gong, L., Tidwell, T. T Can. J. Chem. 1991, 69, 138-145. Andraos, J.; Kresge, A. J.; Schepp, N. P. Can J. Chem 1995, 73, 539-543.
25. Hine, J., Skoglund, M. J. J. Org. Chem. 1982, 47, 4758-4766.
26. (a) Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273-279.
27. (b) Allen, A. D ; Andraos, J.; Kresge, A. J.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc 1992, 114, 1878-1879. Andraos, J.; Kresge, A. J. J. Am. Chem. Soc. 1992, 114, 5643-5646
28. (b) Allen, A. D ; Andraos, J.; Kresge, A. J.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc 1992, 114, 1878-1879. Andraos, J.; Kresge, A. J. J. Am. Chem. Soc. 1992, 114, 5643-5646
29. Allen, A. D.; McAllister, M. A.; Tidwell, T T. Tetrahedron Lett 1993, 34, 1095-1098.
30. (a) Gold, V.; Grist, S. J Chem. Soc., Perkin Trans. 2 1972, 89-95.
31. (b) Kresge, A. J., More O'Ferrall, R. A , Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E. Lee, C. C., Eds.; Elsevier, Amsterdam, 1987; Vol. 7, pp 177-273.
32. (c) Washabaugh, M. W.; Jencks, W. P J. Am. Chem. Soc. 1989, 111, 683-692.
33. Bates, R. G. Determination of pH Theory and Practice; Wiley: New York. 1973, p 49.
34. Loudon, G. M. J. Chem. Educ. 1991, 68, 973-984.
35. 19
36. Covington, A K , Robinson, R. A , Bates, R. G. J. Phys Chem. 1966, 70, 3820-3824 Gold, V ; Lowe, B M J. Chem. Soc. (A) 1967, 936-943.
37. Covington, A K , Robinson, R. A , Bates, R. G. J. Phys Chem. 1966, 70, 3820-3824 Gold, V ; Lowe, B M J. Chem. Soc. (A) 1967, 936-943.
38. Laughton, P M.; Robertson, R E In Solute-Solvent Interactions; Coetzee, J F , Ritchie, C D., Eds , Marcel Dekker: New York, 1969, pp 399-538
39. Keeffe, J R , Kresge, A. J In The Chemistry of Enols: Rappoport, Z , Ed : Wiley New York, 1990; pp 399-480.
40. Chiang, Y., Kresge, A J.; Walsh, P. A. Z. Naturforsch. 1989, 44a, 406-412
41. 16
42. Bunting, J. W.; Kanter, J. P. J. Am. Chem. Soc. 1993, 115, 11705-11715.
43. Pedersen, K. J. J. Phys. Chem. 1934, 38, 993-998.
44. For a brief review of the evidence regarding vinyl ether hydrolysis, see: Kresge, A. J. Acc. Chem Res. 1987, 20, 364-370.
45. Kresge, A. J.; Sagatys, D. S., Chen, H. L. J. Am. Chem. Soc 1977, 99, 7228-7233.
46. Kresge, A. J.; Ubysz, D. J. Phys. Org. Chem. 1994, 7, 316-322.
47. 30 31
48. Tee, O. S.; Iyengar, N. R. J. Org Chem 1985, 50, 4468-4473
49. (a) Tee, O. S.; Iyengar, N. R., Bennett, J. M. J. Org. Chem. 1986, 51 2585-2589.
50. (b) Tee, O. S.; Iyengar, N. R. Can. J Chem. 1987, 65, 1714-1718