Nucleophilic substitution and Claisen rearrangement reactions of model fluoroalkenes of general structure R-CF=CF-CF3.
Fluoroalkenes of general structure R-CF=CF-CF3 (2a, R = cyclopentyl and 2b, R = cyclohexyl), prepared in high yield in two steps from hexafluoropropene and the appropriate cycloalkane, react with oxygen, carbon, and hydrogen nucleophiles to give R-CX=CF-CF3 derivatives (X = H, OR, R, Ar). Reaction of fluoroalkenes 2a and 2b with allylic alkoxides gave products arising from Claisen rearrangement, providing access to keto-alkenes bearing >CFCF3 units in mid-aliphatic chain positions.
Cooper
J A
JA
University of Durham, Department of Chemistry, South Road, Durham, DH1 3LE, UK.
Olivares
C M
CM
Sandford
G
G
D005461:Fluorine; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D006845:Hydrocarbons, Fluorinated; D005461:Fluorine