Stereoelectronic effects in negatively and positively (protonated) charged species. Ab initio studies of the gauche effect in 1,4-dioxa systems

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 558-561

  Ganguly, Bishwajit ^a   Fuchs, Benzion ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXANE DERIVATIVE;

ARTICLE; CONFORMATION; ISRAEL; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034723303     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991012+     Document Type: Article

References (35)

1. Ganguly, B.; Fuchs, B. J. Org. Chem. 1997, 62, 8892.
2. (a) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer: Berlin, 1983.
3. (b) Kirby, A. In The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. G., Ed.; ACS Symposium Series No. 539; American Chemical Society: Washington, DC, 1993; Chapter 4.
4. (c) Pinto, B. M.; Leung, R. Y. N. Ibid., Chapter 8.
5. (d) Juaristi, E. J. Chem. Educ. 1979, 56, 438.
6. (e) Nelsen, S. F. Acc. Chem. Res. 1978, 11, 14.
7. (f) Zefirov, N. S.; Gurvich, L. G.; Shashkov, A. S.; Krimer, M. Z.; Vorob'eva, E. A. Tetrahedron 1976, 32, 1211.
8. (a) Andrews, C. W.; Rodebaugh, R.; Fraser-Reid, B. J. Org. Chem. 1996, 61, 5280.
9. (b) Kennedy, J.; Wu, J.; Drew, K.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 1997, 119, 8933.
10. (c) Liras, J. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1997, 119, 8191.
11. (a) Senderowitz, H.; Golender, L.; Fuchs, B. Tetrahedron 1994, 50, 9707 and references therein.
12. (b) Senderowitz, H.; Fuchs, B. THEOCHEM 1997, 395/396, 123.
13. (a) Wolfe, S. Acc. Chem. Res. 1972, 5, 102.
14. (b) Wolfe, S.; Rauk, A.; Tel, L. M.; Csizmadia, I. G. J. Chem. Soc. B 1971, 136.
15. (a) Epiotis, N. D.; Cherry, W. J. Chem. Soc., Chem. Commun. 1973, 278.
16. (c) Epiotis, N. D. J. Am. Chem. Soc. 1973, 95, 3087.
17. (b) Epiotis, N. D.; Yates, R. L.; Larson, J. R.; Kirmaier, C. R.; Bernardi, F. J. Am. Chem. Soc. 1977, 99, 8379.
18. Wiberg, K. B.; Murcko, M. A.; Laiding, K. E. J. Phys. Chem. 1990, 94, 6956.
19. (a) Craig, N. C.; Chen, A.; Suh, K. H.; Klee, S.; Mellau, G. C.; Winnewisser, B. P.; Winnewisser, M. J. Am. Chem. Soc. 1997, 119, 4789.
20. (b) Engkvist, O.; Karlstrom, G.; Widmark, P. O. Chem. Phys. Lett. 1997, 265, 19.
21. (a) Jaffe, R. L.; Smith, G. D.; Yoon, D. Y. J. Phys. Chem. 1993, 97, 12745.
22. (b) Tsuzuki, S.; Uchimaru, T.; Tanabe, K.; Hirano, T. J. Phys. Chem. 1993, 97, 1346.
23. (c) Williams, D. J.; Hall, K. B. J. Phys. Chem. 1996, 100, 8224.
24. (d) Müller-Plathe, F.; van Gunsteren, W. F., Macromolecules 1994, 27, 6040.
25. (a) Chang, Y.-P.; Su T.-M.; Li, T.-W.; Chao, I. J. Phys. Chem. A 1997, 101, 6107.
26. (b) Yeh, T.-S.; Chang, Y.-P.; Su, T.-M.; Chao, I. J. Phys. Chem. 1994, 98, 8921.
27. Linden, A.; Rüchardt, Chr.; Beckhaus, H.-D.; Verevkin, S. P.; Ganguly, B.; Fuchs, B. J. Org. Chem. 1998, 63, 8205.
28. Chandrasekhar, J.; Andrade, J. G.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 5619.
29. Dewar, M. J. S.; Dieter, K. M. J. Am. Chem. Soc. 1986, 108, 8075.
30. Gaussian 94: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.;Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J., Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1995.
31. Antolinez, S.; Lopez, J. C.; Alonso, J. L. Angew. Chem-Int. Ed. 1999, 38, 1772
32. (a) Consalvo, D.; Spoerel, U. Chem. Phys. Lett. 1998, 297, 543.
33. (b) Spoerel, U.; Stahl, W.; Caminati, W.; Favero, P. G. Chem. Eur. J. 1998, 4, 1974.
34. (a) Caminati, W.; Moreschini, P.; Rossi, I.; Favero, P. G. J. Am. Chem. Soc. 1998, 120, 11144.
35. (b) Caminati, W.; Dell'Erba, A.; Melandri, S.; Favero, P. G. J. Am. Chem. Soc. 1998, 120, 5555.