Solvolytic reactivity of heptafluorobutyrates and trifluoroacetates

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 5927-5933

  Denegri, Bernard ^a   Kronja, Olga ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; PULSE CODE MODULATION; SOLVENTS;

AROMATIC RINGS; CHARGE SEPARATIONS; CHEMICAL EQUATIONS; ELECTRON WITHDRAWING GROUP; LEAVING GROUPS; NEGATIVE CHARGE; SLOPE PARAMETER; TRIFLUOROACETATES;

NEGATIVE IONS;

ACETONE; ALCOHOL; BUTYRIC ACID DERIVATIVE; METHANOL; TRIFLUOROACETIC ACID; FLUOROCARBON; PERFLUOROBUTYRIC ACID; SOLVENT;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL REACTION; ELECTRON; SEPARATION TECHNIQUE; SOLVOLYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; KINETICS; QUANTUM THEORY;

FLUOROCARBONS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; SOLVENTS; TRIFLUOROACETIC ACID;

EID: 70349095533     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900852u     Document Type: Article

References (25)

1. Creary, X.; O'Donnell, B. D.; Vervaeke, M. J. Org. Chem. 2007, 72, 3360-3368.
2. Bentley, T. W.; Roberts, K. J. Chem. Soc., Perkin Trans. 2 1989, 1055-1060.
3. (a) Takeuchi, K.; Yoshida, M.; Ohga, Y.; Tsugeno, A.; Kitagawa, T. J. Org. Chem. 1990, 55, 6063-6065.
4. (b) Takeuchi, K.; Kitagawa, T.; Ohga, Y.; Yoshida, M.; Akiyama, F.; Tsugeno, A. J. Org. Chem. 1992, 57, 280-291.
5. Farcasiu, D.; Jaehme, J.; Rüchardt, C. J. Am. Chem. Soc. 1985, 107, 5717-5722.
6. (a) Winter, J. G.; Scot, J. M. W. Can. J. Chem. 1968, 48, 2886.
7. (b) Albery, W. J.; Robinson, B. H. Trans. Faraday Soc. 1969, 65, 890.
8. (a) Denegri, B.; Streiter, A.; Jurić, S.; Ofial, A. R.; Kronja, O.; Mayr, H. Chem. - Eur. J. 2006, 12, 1648-1656.
9. (b) Correction: Denegri, B.; Streiter, A.; Jurić, S.; Ofial, A. R.; Kronja, O.; Mayr, H. Chem. - Eur. J. 2006, 12, 5415-5415
10. (c) Denegri, B.; Ofial, A. R.; Jurić, S.; Streiter, A.; Kronja, O.; Mayr, H. Chem. - Eur. J. 2006, 12, 1657-1666.
11. (d) Denegri, B.; Minegishi, S.; Kronja, O.; Mayr, H. Angew. Chem., Int. Ed. 2004, 43, 2302-2305.
12. Bentley, T. W. Chem. - Eur. J. 2006, 12, 6514-6520.
13. Richard, J. P.; Toteva, M. M.; Amyes, T. L. Org. Lett. 2001, 3, 2225-2228.
14. (a) Okamoto, Y.; Brown, H. C. J. Org. Chem. 1957, 22, 485-494.
15. (b) Tsuno, Y.; Fujio, M. Adv. Phys. Org. Chem. 1999, 32, 267-385.
16. (a) McLennan, D. J.; Martin, P. L. Aust. J. Chem. 1979, 32, 2361-2370.
17. (b) McLennan, D. J. Tetrahedron 1978, 34, 2321-2341.
18. (c) McLennan, D. J.; Martin, P. L. J. Chem. Soc., Perkin Trans. 2 1982, 1999-2105.
19. (a) Lomas, J. S.; Dubois, J. E. J. Org. Chem. 1975, 40, 3303-3304.
20. (b) Lomas, J. S. Tetrahedron Lett. 1978, 20, 1783-1786.
21. Denegri, B.; Kronja, O. J. Phys. Org. Chem. 2009, 22, 495-503.
22. Denegri, B.; Kronja, O. J. Org. Chem. 2007, 72, 8427-8433.
23. Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121-159.
24. Moroi, Y.; Yano, H.; Yonemitsu, T. Bull. Chem. Soc. Jpn. 2001, 74, 667-672.
25. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, Revision D.02; Gaussian, Inc., Wallingford, CT, 2004