Generation of doubly trifluoromethylsubstituted carbocations: Synthesis of α,α-Bis(trifluoromethyl)benzylamines

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4881-4884

  Nesi, Marcella ^a   Brasca, Maria Gabriella ^a   Longo, Antonio ^a   Moretti, Walter ^a   Panzeri, Achille ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLAMINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030975053     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01018-6     Document Type: Article

References (17)

1. (a) Organofluorine Chemicals and their Industrial Applications; Banks, R.E. Ed.; Ellis Horwood Ltd.: Chichester, 1979.
2. (b) Biomedicinal Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y. Eds.; Kodansha Ltd.: Tokyo; Elsvier Biomedical Press: Amsterdam, 1982.
3. (a) A. Panzeri; M. Nesi; E. di Salle Patent WO 9514709; Chem. Abstr. 1995, 123, 228635.
4. (b) A. Panzeri; M. Nesi; E. di Salle Patent WO 9403474; Chem. Abstr. 1994, 121, 83749.
5. (c) A. Panzeri; M. Nesi; E. di Salle Patent WO 9403475; Chem. Abstr. 1994, 121, 57781.
6. (d) Giudici, D.; Briatico, G.; Cominato, C.; Zaccheo, T.; Iehlè, C.; Nesi, M.; Panzeri, A. and di Salle, E. J. Steroid Biochem. Mol. Biol. 1996, 58, 299-305.
7. (a) Middleton, W. J. and Krespan, C.G. J. Org. Chem. 1965, 30, 1398.
8. (b) Gale, D. M. and Krespan, C. G. J. Org. Chem. 1968, 33, 1002.
9. Allen, A. D.; Kanagasabapathy, V. M. and Tidwell, T. T. J. Am. Chem. Soc. 1986, 108, 3470-3474.
10. Balderman, D.; Kalir, A. Synthesis, 1978, 24.
11. (a) Krimen, L.I. and Cota, D. J.; Organic Reactions 1969, Vol. 17.
12. (b) Bishop, R. Comprehensive Organic Synthesis, 1.9.
13. Creary, X. Chem. Rev. 1991,. 91, 1625-1676, and cit. lit.
14. Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1982, 85, and cit. lit.
15. 2O. The potassium salt is then reacted with triflic anhydride.
16. 2O of the acidic phase furnishes amine 1b in quantitative yield.
17. N2 type reactions of α-trifluoromethylated alcohols: Hagiwara, T.; Tanaka, K. and Fuchikami, T. Tetrahedron Lett. 1996, 37, 8187-8190.