Reductive defluorination of polyfluoroarenes by zinc in aqueous ammonia

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3765-3768

  Laev, Sergey S ^a   Shteingarts, Vitalij D ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; DEFLUORINATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030992553     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00730-2     Document Type: Article

References (21)

1. Vorozhtsov, N. N.; Platonov, V. E.; Yakobson, G. G. Izv.Akad. Nauk SSSR, Ser. Khim. 1963, 1524.
2. Yakobson, G. G.; Shteingarts, V. D.; Vorozhtsov, N. N. Izv.Akad. Nauk SSSR, Ser. Khim. 1964, 1551.
3. Filler, G. J. Chem. Soc. 1965, 6264-6267.
4. Hudlicky, M. Reduction in organic chemistry; Ellis Horwood Limited: Chichester, 1984.
5. Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373-431.
6. Krasnov, V. I.; Platonov, V. E. Zh. Org. Khim. 1993, 29, 1078-1079.
7. Krasnov, V. I.; Platonov, V. E. Zh. Org. Khim. 1994, 30, 1271-1275.
8. Masahiko, Y.; Masanori, S.; Shusuke, N. JP-02115156, Chem. Abstr. 1990, 113, 97208.
9. Laev, S. S.; Shteingarts, V. D.; Bilkis, I. I. Tetrahedron Lett. 1995, 36, 4655-4658.
10. Kishan, L. H.; Kanchan, G. Tetrahedron Lett. 1986, 27, 1371.
11. Hu, Ch.-M.; Long, F.; Xu, Ze-Qi. J. Fluorine Chem. 1990, 48, 29.
12. Shteingarts, V. D.; Kobrina, L. S.; Bilkis, I. I.; Starichenko, V. F. Chemistry of Polyfluoroarenes: Reaction Mechanisms and Intermediates; Nauka: Novosibirsk, 1991 (in Russian).
13. 19F NMR and IR spectra were identical to those of authentic specimen.
14. Drakesmith, F. G. J. Chem. Soc., Perkin Trans. 1 1972, 184-189.
15. 19F NMR data).
16. 19F NMR and IR spectra were in accordance with literature NMR (see ref. 14) and IR data (see: Aroskar, E. V.; Brown, P. J. N.; Plevey, R. G.; Stephens, R. J. Chem. Soc., C 1968, 1569-1575).
17. Banks, R E.; Burgess, J. E.; Cheng, W. M.; Haszeldine, R. N. J. Chem. Soc., 1965, 575-581.
18. 19F NMR spectra were identical to literature ones (see: Lee, J.; Orrell, K. G. J. Chem. Soc., 1965, 582-594).
19. 2: C, 47.16; H, 0.72; F, 40.69. Found: C, 47.43; H, 0.82; F, 40.56.
20. 19F NMR data).
21. Kiplinger, J. L.; Richmond, T. G. J. Chem. Soc., Chem. Commun. 1996, 1115-1116.