Acid-catalyzed solvolysis of allylic ethers and alcohols. Competing elimination and substitution via a thermodynamically 'stable' carbocation

Journal of the American Chemical Society

Volumn 120, Issue 26, 1998, Pages 6512-6517

  Pirinccioglu, Necmettin ^a   Thibblin, Alf ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ETHER DERIVATIVE;

ARTICLE; CATALYSIS; DRUG HYDROLYSIS; ENTHALPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; REACTION ANALYSIS; TEMPERATURE; THERMODYNAMICS;

EID: 0032496947     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9807800     Document Type: Article

References (33)

1. Thibblin, A. Chem. Soc. Rev. 1993, 22, 427.
2. (a) Thibblin, A.; Sidhu, H. J. Am. Chem. Soc. 1992, 114, 7403.
3. (b) Meng, Q.; Thibblin, A. Submitted.
4. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1373.
5. Boyd, D. R.; McMordie, R. A. S.; Sharma, N. D.; More O'Ferrall, R. A.; Kelly, S. C. J. Am. Chem. Soc. 1990, 112, 7822.
6. More O'Ferrall, R. A.; Rao, S. N. Croat. Chem. Acta 1992, 65, 593.
7. (a) Boyd, D. R.; McMordie, R. A. S.; Sharma, N. D.; Dalton, H.; Williams, P.; Jenkins, R. O. J. Chem. Soc., Chem. Commun. 1989, 339.
8. (b) Boyd, D. R.; Hand, M. V.; Sharma, N. D.; Chima, J.; Dalton, H.; Sheldrake, G. N. J. Chem. Soc., Chem. Commun. 1991, 1630.
9. (c) Boyd, D. R.; Dorrity, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666.
10. (a) Sneen, R. A.; Felt, G. R.; Dickason, W. C. J. Am. Chem. Soc. 1973, 95, 638.
11. (b) Thibblin, A. J. Chem. Soc., Perkin Trans. 2 1987, 1629.
12. (C) Katritzky, A. R.; Brycki, B. E.; J. Phys. Org. Chem. 1988, 1, 1 and references therein.
13. (d) Szele, I.; Zollinger, H. J. Am. Chem. Soc. 1978, 100, 2811.
14. (e) Hashida, Y.; Landells, R. G. M.; Lewis, G. E.; Szele, I.; Zollinger, H. J. Am. Chem. Soc. 1978, 100, 2816.
15. (f) Thibblin, A. J. Chem. Soc., Chem. Commun. 1990, 697.
16. (g) Thibblin, A. J. Org. Chem. 1993, 58, 7427.
17. (h) Thibblin, A. J. Phys. Org. Chem. 1993, 6, 287.
18. (i) Thibblin, A.; Sidhu, H. J. Phys. Org. Chem. 1993, 6, 374.
19. (j) Bleasdale, C.; Golding, B. T.; Lee, W. H. L.; Maskill, H.; Riseborough, J.; Smits, E. J. Chem. Soc., Chem. Commun. 1994, 93.
20. (k) Sidhu, H.; Thibblin, A. J. Phvs. Org. Chem. 1994, 7, 578.
21. (l) Thibblin, A.; Saeki, Y. J. Org. Chem. 1997, 62, 1079.
22. Gagneux, A.; Winstein, S.; Young, W. G. J. Am. Chem. Soc. 1960, 82, 5956.
23. (a) Schubert, W. M.; Keefe, J. R. J. Am. Chem. Soc. 1972, 94, 559.
24. (b) Modena, G.; Rivetti, F.; Scorrano, G.; Tonellato, U. J. Am. Chem. Soc. 1977, 99, 3392.
25. Toteva, M. M.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 11445.
26. Slow nucleophilic addition has previously been reported for α-car-bonyl-and α-thiocarbonyl-substituted benzyl carbocations: Richard, J. P.; Lin, S.-S.; Buccigross, J. M.; Amyes, T. L. J. Am. Chem. Soc. 1996, 118, 12603.
27. McClelland, R. A. Tetrehedron 1996, 52, 6823.
28. (a) Rosenberg, A. M.; Sneen, R. A. J. Am. Chem. Soc. 1961, 83, 900.
29. (b) Thibblin, A. J. Chem. Soc., Perkin Trans. 2 1986, 313.
30. Bunton, C. A.; Carrasco, N.; Cully, N.; Watts, W. E. J. Chem. Soc., Perkin Trans. 2 1980, 1859.
31. Moss, R. J.; Rickborn, B. J. Am. Chem. Soc. 1986, 51, 1992.
32. (a) Bamberger, E.; Lodter, W. Justus Leibigs Ann. Chem. 1895, 288, 100.
33. (b) Jeffrey, A. M.; Jerina, D. M. J. Am. Chem. Soc. 1972, 94, 4048.