FLUORIDE-CATALYZED MICHAEL-ADDITION OF 2,2,2-TRIFLUORONITROALKANES TO ACTIVATED MONDOLEFINS

The fluoride catalyzed addition of the 2,2,2,-trifluoronitroalkanes CF3CH2NO2 (Ia) and CF3CH(CH3)NO2 (Ib) to activated carbon-carbon double bonds was applied to the synthesis of functionalized trifluoromethyl nitroalkanes CF3C(R)NO2C(R1R2)CH(R3) Y (II) (R=H, CH3). The influence of steric and electronic factors on the formation of the adducts (II) was investigated via systematic variation of the activating group Y, and the substituents (R1, R2, R3) on the double bond. The trifluoromethyl nitroalkanes reported represent a class of compounds which are possible intermediates for the synthesis of biologically active compounds. © 1990.