NITROXIDE CHEMISTRY .14. REACTIONS OF TRIFLUOROMETHYL 2,3-DIMETHYLBUT-3-EN-2-YL AND TRIFLUOROMETHYL 2,3-DIMETHYLBUT-2-YL NITROXIDES

The nitroxide CF3N(Ȯ)CMe2CMeCH2 abstracts the aldehydic hydrogen from benzaldehyde, yielding the benzoyl compound PhCO2N(CF3)CMe2CMeCH2 (82%), the benzylic hydrogen from cumene, yielding PhCMe2ON(CF3)CMe2CMeCH2 (80%), and the methylene group hydrogen from fluorene, oxidises benzoin to benzil, and hydroquinol to quinone, attacks the Si'&'2.sbnd;H bond of trimethylsilane, and adds to tetrafluoroethylene to give the compound R1N(CF3)OCF2CF2ON(CF3)R1 (R1 = CMe2CMeCH2, 97%), and to hexafluoropropene to give the 2:1-adduct. In a similar manner, the nitroxide CF3N(Ȯ)CMe2CHMe2 adds to tetrafluoroethylene to give the compound R2N(CF3)OCF2CF2ON(CF3)R2 (R2 = CMe2CHMe2, 75%) and to hexafluoropropene to give a similar adduct (71%), and abstracts a benzylic hydrogen from toluene. © 1979.