POLYHALOETHERS FROM REACTION OF FLUOROALCOHOLS AND HALOOLEFINS

The base-induced addition of several fluorinated alcohols to a variety of cyclic and acyclic polyhaloolefins is described. The general reaction scheme is: RCF2CH(R′)OH + CF2 = CXY → RCF2CH2(R′)OCF2CXYH, where R is F or fluoroalkyl, R′ is H, alkyl, or fluoroalkyl, X is F, Cl, Br, or H, and Y is F, Cl, fluoroalkyl, or H. With perfluorocydoolefins, an addition-elimination mechanism gave rise to unsaturated products containing one, two, or three fluoroalkoxy groups, depending on the reaction conditions. Twenty novel fluorinated ethers were thus prepared. NMR spectroscopy was used in many instances to confirm product structure. All new data thus acquired are presented. © 1969, American Chemical Society. All rights reserved.