Anomeric effect enhancement in C-5-substituted 2-methoxytetrahydropyrans

Journal of Molecular Structure

Volumn 412, Issue 1-2, 1997, Pages 51-58

  Srivastava, R M ^a,b   Pavao A C ^a   Seabra, G M ^a   Brown, R K ^b  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

2 Methoxytetrahydropyran; AMI calculations; Anomeric effect; Conformation; HF 6 31g** basis set

Indexed keywords

EID: 0030759356     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(97)00001-X     Document Type: Article

References (37)

1. A.J. Kirby, The Anomeric Effect and Related Stereoeletronic Effects at Oxygen, Springer, New York, 1983.
2. E. Juaristi, G. Cuevas, Tetrahedron, 48 (1992) 5019; The Anomeric Effect, CRC Press, Inc., Boca Raton, 1995.
3. E. Juaristi, G. Cuevas, Tetrahedron, 48 (1992) 5019; The Anomeric Effect, CRC Press, Inc., Boca Raton, 1995.
4. C.B. Anderson, D.T. Sepp. Chem. Ind. (London), (1964) 2054.
5. G.E. Booth, R.J. Ouellette. J. Org. Chem., 31 (1966) 544.
6. C.B. Anderson, D.T. Sepp. Tetrahedron, 24 (1968) 1707.
7. E.L. Eliel, C.A. Giza, J. Org. Chem., 33 (1968) 3754.
8. G.O. Pierson, O.A. Runquist. J. Org. Chem., 33 (1968) 2572.
9. F. Sweet, R.K. Brown. Can. J. Chem., 46 (1968) 1543.
10. H. Booth, J.M. Dixon, S.A. Readshaw, Tetrahedron, 48 (1992) 6151.
11. J.P. Praly, R.U. Lemieux, Can. J. Chem., 65 (1987) 213, and references cited therein.
12. M.J.S. Dewar, E.G. Zoebisch, E.F. Heally, J.J.P. Stewart, J. Am. Chem. Soc., 107 (1985) 3902.
13. J.J.P. Stewart, J. Comp.-Aided Mol. Design, 4 (1990) 1.
14. MOPAC 93-00 Manual, J.J.P. Stewart, Fujitsu Limited, Tokyo, Japan, 1993.
15. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Defress, J. Baker, J.J.P. Stewart, J.A. Pople, GAUSSIAN 92, Revision E.1, Gaussian, Inc., Pittsburgh, PA, 1992.
16. P. Pulag, in H.F. Shaefer (Ed.), Modern Theoretical Chemistry, Plenum, New York, Vol. 4, 1977.
17. S.S. Hall, G.F. Weber, A.J. Duggan. J. Org. Chem., 43 (1978) 667.
18. M. Gelin, Y. Bahurel, G. Descotes. Bull. Soc. Chim. Fr., (1970) 3723.
19. R.M. Srivastava, R.K. Brown. Can. J. Chem., 48 (1970) 2334.
20. R.U. Lemieux, A.A. Paira, J.C. Martin, K.A. Watanabe. Can. J. Chem., 47 (1969) 4427.
21. G. Descotes, D. Sinou, J.-C. Martin. Bull. Soc. Chim. Fr., (1970) 3730.
22. C. Monneret, R. Gagnet, J.-C. Florent, J. Carbohyd. Chem., 6 (1987) 221.
23. A.M.A. Souza, M.S. Thesis, 1986, Universidade Federal de Pernambuco, Recife.
24. C. Monneret, C. Conreur, Q. Khuong-Huu, Carbohyd. Res., 65 (1978) 35.
25. E.L. Eliel, M.H. Gianni, Tetrahedr. Lett., (1962) 97.
26. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983.
27. H. Booth, K.A. Khedhair. J. Chem. Soc., Chem. Commun. (1985) 467.
28. H. Booth, T.B. Grindley, K.A. Khedhair, J. Chem. Soc., Chem. Commun., (1982) 1047.
29. R.U. Lemieux, Pure Appl. Chem., 25 (1971) 527.
30. G. Wood, E.P. Woo, M.H. Miskow, Can. J. Chem., 47 (1969) 429, and references cited therein.
31. K.B. Wiberg, M.A. Murcko, J. Am. Chem. Soc., 111 (1989) 4821.
32. I. Tvaroska, T. Bleha, in R.S. Tipson and D. Horton (Eds.), Advances in Carbohydrate Chemistry and Biochemistry, Academic Press, San Diego, 1989, pp. 75-81, and references therein.
33. I. Tvaroska, T. Kozar, Carbohydr. Res., 90 (1981) 173.
34. R.J. Woods, W.A. Szarek, V.H. Smith, Jr., J. Chem. Soc., Chem. Commun., (1991) 334.
35. O.N. Ventura, E.L. Coitiño, A. Lledós, J. Bertrán, J. Mol. Struc. (Theochem), 187 (1989) 55.
36. G. Buemi, F. Zuccarello, A. Raudino, J. Mol. Struc. (Theochem), 164 (1988) 379.
37. R.J. Woods, R.A. Dwek, C.J. Edge, B. Fraser-Reid, J. Phys. Chem., 99 (1995) 3832.