Kinetic study on denomination of vic-dibromides with trivalent phosphorus compounds

Heteroatom Chemistry

Volumn 12, Issue 4, 2001, Pages 217-222

  Yasui, Shinro ^a  

^a TEZUKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; ATOMS; BROMINE; DEHALOGENATION; ELECTRON ENERGY LEVELS; ELECTRON MOBILITY; ELECTRON TRANSITIONS; OLEFINS; REACTION KINETICS; REDUCTION; STEREOCHEMISTRY;

BROMOPHILICITY; CARBOPHILICITY; DEBROMINATION; DIBROMIDES; ELECTRON RELEASING SUBSTITUENTS; ELECTRONIC CHARACTER; ELIMINATION; NUCLEOPHILIC ATTACK;

PHOSPHORUS COMPOUNDS;

EID: 0034980191     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/hc.1035     Document Type: Article

References (20)

1. Khurana, J. M.; Maikap, G. C. J Org Chem 1991, 56, 2582-2584.
2. Butcher, T. S.; Zhou, F.; Detty, M. R. J Org Chem 1998, 63, 169-176.
3. Butcher, T. S.; Detty, M. R. J Org Chem 1999, 64, 5677-5681.
4. Yang, J.; Bauld, N. L. J Org Chem 1999, 64, 9251-9253.
5. Yasui, S.; Nakamura, K.; Ohno, A. Bull Chem Soc Jpn 1985, 58, 1847-1848.
6. Adam, W.; Arce, J. J Org Chem 1972, 37, 507-508.
7. (a) O'Connell, K. M.; Evans, D. H. J Am Chem Soc 1983, 105, 1473-1481;
8. (b) Lexa, D.; Savéant, J.-M.; Schäfer, H. J.; Su, K.-B.; Vering, B.; Wang, D. L. J Am Chem Soc 1990, 112, 6162-6177.
9. Yasui, S. Rev Heteroat Chem 1995, 12, 145-161 and references cited therein.
10. Yasui, S.; Tsujimoto, M.; Shioji, K.; Ohno, A. Chem Ber Recueil 1997, 130, 1699-1707.
11. Speziale, A. J.; Tung, C. C. J Org Chem 1963, 28, 1353-1357.
12. Tung, C. C.; Speziale, A. J. J Org Chem 1963, 28, 1521-1523.
13. Schroeder, J. P.; Tew, L. B.; Peters, V. M. J Org Chem 1970, 35, 3181-3184.
14. Devlin, C. J.; Walker, B. J. J Chem Soc Perkin 1, 1972, 1249-1253.
15. Yasui, S.; Tsujimoto, M.; Okamura, M.; Ohno, A. Bull Chem Soc Jpn 1998, 71, 927-932.
16. Debromination of 2z with tris (2,6-dimethoxyphenyl)phosphine la takes place undoubtedly through a nucleophilic mechanism because la is an efficient nucleophile but a poor electron donor [16]. Therefore, the fact that the point for the reaction with la fits the linear line given in Figure 2 confirms the nucleophilic mechanism occurring in the debromination also with other phosphorus compounds Ib-h.
17. Yasui, S.; Tsujimoto, M.; Itoh, K.; Ohno, A. J Org Chem 2000, 65, 4715-4720.
18. Ho, T.-L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic: New York, 1977.
19. (a) Borowitz, I. J.; Kirby, K. C., Jr.; Rusek, P. E.; Casper, E. W. R. J Org Chem 1971, 36, 88-97;
20. (b) Borowitz, I. J.; Farnes, H.; Lord, E.; Yee, K. C. J Am Chem Soc 1972, 94, 6817-6822.