Hydrolysis of cyclic orthoesters: Experimental observations and theoretical rationalization

Tetrahedron

Volumn 52, Issue 47, 1996, Pages 14841-14854

  Li, Shigui ^a   Dory, Yves L ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANOL DERIVATIVE;

ARTICLE; CALCULATION; HYDROLYSIS; ISOTOPE LABELING; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16144363866     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00915-5     Document Type: Article

References (12)

1. 1. Deslongchamps, P.; Chênevert, R.; Taillefer, R.J.; Moreau, C.; Saunders, J.K. Can. J. Chem. 1975, 53, 1601.
2. 2. Deslongchamps, P.; Lessard, J.; Nadeau, Y. Can. J. Chem. 1985, 63, 2485.
3. 3. Deslongchamps, P.; Guay, D.; Chênevert, R. Can. J. Chem. 1985, 63, 2493.
4. 4. Deslongchamps, P.; Dory, Y.L.; Li, S. Heterocycles 1996, 42 (2), 617.
5. 5. Li, S.; Kirby, A.J.; Deslongchamps, P. Tetrahedron Lett. 1993, 34, 7757.
6. 6. Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902.
7. 7. Bunton, C.A.; De Wolfe, R.H. J. Org. Chem. 1965, 30, 1371.
8. 8. R. Eliason and M.M. Kreevoy. J. Am. Chem. Soc. 1978, 100, 7037.
9. 9. Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon, M.S.; Jensen, J.H.; Koseki, S.; Matsunaga, N.; Nguyen, K.A.; Su, S.J.; Windus, T.L.; Dupuis, M.; Montgomery, J.A. J. Comput. Chem. 1993, 14, 1347.
10. 10. Computational procedure: All the calculations were done at the RHF level using MOPAC 6.00 (Stewart, J.J.P. QCPE No. 455) in the case of AM1 optimization and GAMESS for 3-21G calculations. The ground state structures were characterized by zero imaginary frequency and the transition state structures by only one imaginary frequency. The IRC studies were carried out with AMPAC 5.0 (Semichem, 7128 Summit, Shawnee, KS 66216).
11. 11. Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry, Baldwin, J. E., Ed.; Organic Chemistry Series, Vol. I; Pergamon Press: Oxford, England, 1983. p. 31.
12. 12. Li, S.; Deslongchamps, P. Tetrahedron Lett. 1994, 353, 5641.