Exclusive β-substitution in the reaction of octafluoronaphthalene with secondary amines

European Journal of Organic Chemistry

Volumn , Issue 4, 2004, Pages 766-769

  Sorokin, Vladimir I ^a   Ozeryanskii, Valery A ^a   Pozharskii, Alexander F ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

Arenes; Naphthalene derivatives; Nucleophilic substitution; Protodefluorination

Indexed keywords

1,4,5,8 TETRAFLUORO 2,3,6,7 TETRAKIS(PIPERIDIN 1 YL)NAPHTHALENE; ALUMINUM DERIVATIVE; AMINE; DIMETHYL(ETHYLENE)UREA; DIMETHYLAMINE; FLUORINE DERIVATIVE; LITHIUM DERIVATIVE; NAPHTHALENE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; UREA DERIVATIVE;

AMIDATION; ARTICLE; ATOM; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; SUBSTITUTION REACTION;

EID: 4544276641     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300570     Document Type: Article

References (17)

1. [1a] B. Gething, C. R. Patrick, J. C. Tatlow, J. Chem. Soc. 1962, 186-190.
2. [1b] D. Price, H. Suschitzky, J. I. Hollies, J. Chem. Soc., C 1969, 1967-1973.
3. [1c] J. Burdon, T. W. Rimmington, J. Fluorine Chem. 1985, 27, 257-262.
4. [1d] P. P. Rodionov, O. I. Osina, V. E. Platonov, G. G. Yakobson, Bull. Soc. Chim. Fr. 1986, 986-993.
5. These results are based on charge distribution and anionic localisation energy calculations, made using semiempirical PM3 quantum chemical methods in the MOPAC 6.0 program; J. J. P. Stewart, MOPAC 6.0, Quantum Chemistry Program Exchange, University of Indiana, Bloomington, Indiana, USA.
6. [3a] A. F. Pozharskii, Russ. Chem. Rev. 1998, 67, 1-24.
7. [3b] V. I. Sorokin, V. A. Ozeryanskii, A. F. Pozharskii, Russ. J. Org. Chem. 2002, 38, 699-708.
8. [3c] V. I. Sorokin, V. A. Ozeryanskii, A. F. Pozharskii, Eur. J. Org. Chem. 2003, 496-498.
9. [4a] R. S. Asquith, W. M. Lord, A. T. Peters, F. Wallace. J. Chem. Soc., C 1966, 95-96.
10. [4b] F. I. Abezgauz, S. V. Sokolov, Zh. Org. Khim. 1967, 37, 809-814.
11. [5a] T. Mukhopadhyay, D. Seebach, Helv. Chim. Acta 1982, 65, 385-391.
12. [5b] G. R. Brown, A. J. Foubister, C. A. Roberts, S. L. Wells, R. Wood, Tetrahedron Lett. 2001, 42, 3917-3919.
13. [6a] H. A. Staab, K. Elbl, C. Krieger, Tetrahedron Lett. 1986, 27, 5719-5722.
14. [6b] H. A. Staab, K. Elbl-Weiser, C. Krieger, Eur. J. Org. Chem. 2000, 327-333.
15. [7a] J. F. Bunnet, R. E. Zahler, Chem. Rev. 1951, 49, 273-412.
16. [7b] R. D. Chambers, W. K. R. Musgrave, J. S. Waterhouse, D. L. H. Williams, J. Burdon, W. B. Hollyhead, J. C. Tatlow, J. Chem. Soc., Chem. Commun. 1974, 239-240.
17. [7c] R. K. Atwal, R. Bolton, Aust. J. Chem. 1987, 40, 241-247.