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
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.