Trifluoroacetic acid → Cyclohexyl trifluoroacetate

Reaction equation

[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[F:7][C:8]([F:13])([F:12])[C:9]([OH:11])=[O:10]>[Cu]>[CH:1]1([O:11][C:9](=[O:10])[C:8]([F:13])([F:12])[F:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Procedure

Both experiments with copper metal deposited the white precipitate. During the course of the second experiment, solution samples were taken for analysis. Cyclohexene was found to be the major reaction product (ester/olefin=0.2) which slowly reacted with trifluoroacetic acid to form cyclohexyltrifluoroacetate. Thus, elimination of cyclohexene from a cyclohexyl-copper complex is the predominant reaction pathway under our conditions.