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

Authors
Banks, RE Besheesh, MK Lawrence, NJ Pritchard, RG Tovell, DJ
Citation
Re. Banks et al., 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, CHEM COMMUN, (1), 1999, pp. 47-48
Citations number
13
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
1
Year of publication
1999
Pages
47 - 48
Database
ISI
SICI code
1359-7345(19990107):1<47:NCOPT3>2.0.ZU;2-K
Abstract
Unexpectedly, treatment of perfluoro(2,6-dimethyl-1-azacyclohexene) with 2 equiv. of PhLi in cyclohexane-Et2O at -50 to 40 degrees C gives a good yiel d (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 conve rsion 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.