Preparation and Reactions of 2-Chloroperfluorocyclobutenyl Copper Reagent
2-Chlorotetrafluorocyclobutenyl copper reagent was prepared via copper(I) bromide metathesis from the corresponding zinc reagent which was readily obtained from 1-chloro-2-iodo-3,3,4,4-tetrafluorocyclobutene by the direct reaction with zinc metal in DMF.The copper reagent was used to synthesize alkyl and acyl derivatives of tetrafluorocyclobutene.
Preparation and Reactions of 2-Chloroperfluorocycloalkenylcopper Reagents
1-Chloro-2-iodoperfluorocycloalkenes react with activated zinc powder in dimethylformamide solvent at room temperature to give 2-chloroperfluorocycloalkenylzinc reagents.Treatment of these organozinc reagents with copper(I) bromide at 0 deg C or at room temperature provides a simple route to the corresponding 2-chloroperfluorocycloalkenylcopper.The yield is excellent.These organocopper reagents, which are stable at room temperature in the absence of oxygen and/or moisture, can be used for the production of C-C bonds via reactions with alkyl, aryl and acyl halides.Reaction of these organocopper reagents with acyl halides leads to previously unreported acylated polyfluorocycloalkenes.