The hydrolysis of 4-acyloxy-4-substituted-2,5-cyclohexadienones: Limitations of aryloxenium ion chemistry

Journal of the American Chemical Society

Volumn 127, Issue 22, 2005, Pages 8090-8097

  Novak, Michael ^a   Glover, Stephen A ^b  

^a MIAMI UNIVERSITY   (United States)

^b UNIVERSITY OF NEW ENGLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; DECOMPOSITION; ESTERS; HYDRATION; IONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS; SUBSTITUTION REACTIONS;

ARYLOXENIUM IONS; ESTER HYDROLYSIS; ION CHEMISTRY; PHENOL OXIDATION;

HYDROLYSIS;

4 ACETOXY 4 PHENYL 2,5 CYCLOHEXADIENONE; 4 DICHLOROACETOXY 4 METHYL 2,5 CYCLOHEXADIENONE; BENZENE DERIVATIVE; CYCLOALKENE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

EID: 20444413845     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050899q     Document Type: Article

References (49)

1. (a) Swenton, J. S.; Carpenter, K.; Chen, Y.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1993, 58, 3308-3316.
2. (b) Swenton, J. S.; Callinan, A.; Chen, Y.; Rohde, J. L.; Kerns, M. L.; Morrow, G. L. J. Org. Chem. 1996, 61, 1267-1274.
3. Rieker, A.; Beisswenger, R.; Regier, K. Tetrahedron 1991, 47, 645-654.
4. Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273-282.
5. (a) Rieker, A.; Speiser, B.; Straub, H. Dechema-Monographien 1992, 125, 777-782.
6. (b) Dimroth, K.; Umbach, W.; Thomas, H. Chem. Ber. 1967, 100, 132-141.
7. Rodrigues, J. A. R.; Abramovitch, R. A.; de Sousa, J. D. F.; Leiva. G. C. J. Org. Chem. 2004, 69, 2920-2928.
8. (a) Baesjou, P. J.; Driessen, W. L.; Challa, G.; Reedji, J. J. Am. Chem. Soc. 1997, 119, 12590-12594.
9. (b) Driessen, W. L.; Baesjou, P. J.; Bol, J. E.; Kooijman, H.; Spek, A. L.; Reedjik, J. Inorg. Chim. Acta 2001, 324, 16-20.
10. Kobayashi, S.; Higashimura, H. Prog. Polym. Sci. 2003, 28, 1015-1048.
11. (a) Abramovitch, R. A.; Inbasekaran, M.; Kato, S. J. Am. Chem. Soc. 1973, 95, 5428-5430.
12. (b) Abramovitch, R. A.; Alvernhe, G.; Inbasekaran, M. N. Tetrahedron Lett. 1977, 1113-1116.
13. (c) Abramovitch, R. A.; Inbasekaran, M. N. J. Chem. Soc., Chem. Commun. 1978, 149-150.
14. (d) Abramovitch, R. A.; Alvernhe, G.; Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558-4565.
15. Li, Y.; Abramovitch, R. A.; Houk, K. N. J. Org. Chem. 1989, 54, 2911-2914.
16. (a) Endo, Y.; Shudo, K.; Okamoto, T. J. Am. Chem. Soc. 1977, 99, 7721-7723.
17. (b) Shudo, K.; Orihara, Y.; Ohta, T.; Okamoto, T. J. Am. Chem. Soc. 1981, 103, 943-944.
18. (c) Endo, Y.; Shudo, K.; Okamoto, T. J. Am. Chem. Soc. 1982, 104. 6393-6397.
19. Uto, K.; Miyazawa, E.; Ito, K.; Sakamoto, T.; Kikugawa, Y. Heterocycles 1998, 48, 2593-2600.
20. Hegarty, A. F.; Keogh, J. P J. Chem. Soc., Perkin Trans. 2 2001, 758-762.
21. Novak, M.; Glover, S. A. J. Am. Chem. Soc. 2004, 126, 7748-7749.
22. Vitullo, V. P.; Logue, E. A. J. Org. Chem. 1973, 38, 2265-2267.
23. Rayat, S.; Majumdar, P.; Tipton, P.; Glaser, R. J. Am. Chem. Soc. 2004, 126, 9960-9969.
24. (a) Jameson, C. J. J. Chem. Phys. 1977, 66, 4983-4988.
25. (b) Jiang, C.; Suhadolnik, R. J.; Baker, D. C. Nucleosides Nucleotides 1988, 7, 271-294.
26. Gutsche, C. D.; No, K. H. J. Org. Chem. 1982, 47, 2708-2712.
27. Richard, J. P.; Jencks. W. P. J. Am. Chem. Soc. 1982, 104, 4689-4691;
28. 1982, 104, 4691-4692;
29. 1984, 106, 1383-1396.
30. Novak, M.; Kahley, M. J.; Eiger, E.; Helmick, J. S.; Peters, H. E. J. Am. Chem. Soc. 1993, 115, 9453-9460.
31. (a) Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; Swanegan, L. A. J. Am. Chem. Soc. 1994, 116, 11626-11627.
32. (b) Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; James, T. G. J. Org. Chem. 1995, 60, 8294-8304.
33. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
34. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
35. Glover, S. A.; Novak, M. Can. J. Chem. Submitted.
36. McClelland, R. A.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1995, 117, 4173-4174.
37. Novak, M.; Lin, J. J. Org. Chem. 1999, 64, 6032-6040.
38. (a) Robbins, R. J.; Laman, D. M.; Falvey, D. E. J. Am. Chem. Soc. 1996, 118, 8127-8135.
39. (b) Srivastava, S.; Ruane, P. H.; Toscano, J. P.; Sullivan, M. B.; Cramer, C. J.; Chiapperino, D.; Reed, E. C.; Falvey, D. E. J. Am. Chem. Soc. 2000, 122, 8271-8278.
40. (a) Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116, 4513-4514.
41. (b) Bose, R.; Ahmad, A. R.; Dicks, A. P.; Novak, M.; Kayser, K. J.; McClelland, R. A. J. Chem. Soc., Perkin Trans. 2 1999, 1591-1599.
42. (c) Ren, D.; McClelland, R. A. Can. J. Chem. 1998, 76, 78-84.
43. (d) McClelland, R. A.; Gadosy, T. A.; Ren, D. Can. J. Chem. 1998, 76, 1327-1337.
44. Bordwell, F. G. Acc. Chem. Res. 1970, 3, 281-290.
45. Guthrie, J. P. J. Am. Chem. Soc. 1996, 118, 12878-12885.
46. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161-169.
47. (a) Richard, J. P.; Jencks, W. P. J. Am Chem. Soc. 1984, 106, 1373-1383.
48. (b) Toteva, M. M.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 11434-11445.
49. Wavefunction, Inc.; 18401 Van Karman Ave., Suite 370, Irvine, CA, 92612 U.S.A.