DOI: 10.1039/A807673A
(Paper)
Reference Section for: Chem. Commun., 1999, 47-48
Novel conversion of perfluoro(2,6-dimethyl-1-azacyclohexene) to 3,3,4,4,5-pentafluoro-2,6-diphenyl-2,6-bis(trifluoromethyl)- 1-azabicyclo[3.1.0]hexane
(Note: The full text of this document is currently only available in the PDF Version )
R. Eric Banks, Mohamed K. Besheesh, Nicholas J. Lawrence, Robin G. Pritchard and David J. Tovell
Abstract
Unexpectedly, treatment of perfluoro(2,6-dimethyl-1-azacyclohexene) with 2 equiv. of PhLi in cyclohexane–Et2O at –50 to 40 °C gives a good yield (72%) of (±)-3,3,4,4,5-pentafluoro-2,6-diphenyl-2,6-bis(trifluoromethyl)-1-azabicyclo[3.1.0]hexane 1; the nitranion implicated in this novel conversion can be trapped with sulfuric acid, giving 2,2,4,4,5,5-hexafluoro-2(e),6(e)-diphenyl-2(a),6(a)-bis(trifluoromethyl)piperidine 5.
References
- A. L. Logothetis, J. Am. Chem. Soc., 1965, 87, 749 CrossRef CAS.
- P. G. Gassman and A. Fentiman, J. Org. Chem., 1967, 32, 2388 CrossRef CAS.
- For example, see D. St. C. Black and J. E. Doyle, Aust. J. Chem., 1978, 31, 2247 Search PubMed; E. Breuer and S. Zbaida, J. Org. Chem., 1977, 42, 1904 CAS; J. Mulzer, R. Becker and E. Brunner, J. Am. Chem. Soc., 1989, 111, 7500 CrossRef CAS; E. J. Moran, J. E. Tellew, Z. Zhao and R. W. Armstrong, J. Org. Chem., 1993, 58, 7848 CrossRef CAS.
- S. Ishizaki, M. Ohtsuka, K. Irinoda, K. Kukita, K. Nagaoka and T. Nakashima, J. Antibiot., 1987, 40, 60 CAS.
- R. E. Banks and G. E. Williamson, Chem. Ind (London), 1964, 1864 CAS; R. E. Banks, V. Murtagh and E. Tsiliopoulos, J. Fluorine Chem., 1991, 52, 389 CrossRef CAS; R. E. Banks and V. Murtagh, Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, 6, 3942 Search PubMed.
- R. E. Banks, M. G. Barlow and M. Nickkho-Amiry, J. Fluorine Chem., 1979, 14, 383 CrossRef CAS.
- D. J. Tovell, Ph.D. Thesis, UMIST, 1997; R. E. Banks, M. K. Besheesh, N. J. Lawrence, R. G. Pritchard and D. J. Tovell, publication in preparation.