Fluorinated oxyvinyl compounds and methods of preparing and using same

An oxyvinyl ether selected from the group consisting of:

• __________________________________________________________________________ HCF.sub.2 (CF.sub.2).sub.3 CH.sub.2 O(CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ;
• CF.sub.3 CH.sub.2 O(CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ;
• HCF.sub.2 (CF.sub.2).sub.5 CH.sub.2 O(CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ;
• CCl.sub.3 CH.sub.2 O(CH.sub.2).sub.2 OCH.dbd.CH.sub.2 ;
• - #STR13## - CH.sub.2 .dbd.CHO(CH.sub.2).sub.4 OCH.sub.2 (CF.sub.2).sub.6 CH.sub.2 O(CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ;
• CH.sub.2 .dbd.CHO(CH.sub.2).sub.2 OCH.sub.2 (CF.sub.2).sub.6 CH.sub.2 O(CH.sub.2).sub.2 OCH.dbd.CH.sub.2 ;
• - #STR14## - HOCH.sub.2 (CF.sub.2).sub.6 CH.sub.2 O(CH.sub.2).sub.4 OCH.dbd.CH.sub .2. __________________________________________________________________________

A fluorinated oxyvinyl ester selected from the group consisting of:

• ______________________________________ CF.sub.3 (CF.sub.2).sub.5 CH.sub.2 CH.sub.2 CH[CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ].sub.2 ;
• CCl.sub.3 (CF.sub.2).sub.5 CH.sub.2 CH.sub.2 CH[CO.sub.2 (CH.sub.2).sub. 4 OCH.dbd.CH.sub.2 ].sub.2 ;
• CF.sub.3 (CF.sub.2).sub.9 CH.sub.2 CH.sub.2 CH[CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ].sub.2 ;
• CF.sub.3 (CF.sub.2).sub.7 CH.sub.2 CH.sub.2 CH[CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ].sub.2 ;
• CF.sub.3 (CF.sub.2).sub.3-9 CH.sub.2 CH.sub.2 CH[CO.sub.2 (CH.sub.2).sub. 4 OCH.dbd.CH.sub.2 ].sub.2 ;
• - #STR15## - CF.sub.3 (CF.sub.2).sub.5 CH.sub.2 CH.sub.2 CH[CO.sub.2 CH.sub.3 ][CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ];
• CF.sub.3 (CF.sub.2).sub.7 CH.sub.2 CH.sub.2 CH[CO.sub.2 CH.sub.3 ][CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ];
• CF.sub.3 (CF.sub.2).sub.9 CH.sub.2 CH.sub.2 CH[CO.sub.2 CH.sub.3 ][CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ];
• and CF.sub.3 (CF.sub.2).sub.3-9 CH.sub.2 CH.sub.2 CH[CO.sub.2 CH.sub.3 ][CO.sub.2 (CH.sub.2).sub.4 OCH.dbd.CH.sub.2 ]. ______________________________________

A method for the preparation of a fluorinated ester compound of the formula R.sub.f C.sub.n H.sub.m CH[COOR] where R.sub.f is a fluorinated alkylene moiety of from about 1 to about 12 carbon atoms which may be linear or branch chained, n is a number of from about 2 to about 6, m is a number of n to 2n, and R is cycloalkane or (CH.sub.2).sub.x where x is about 2 to about 10;

• said method comprising:
• a) reacting a carboxylic acid ester of the formula ROOCCH.sub.2 COOR containing an active methylene group with a base which is sufficiently reactive to deprotenate at least one of the hydrogens from the activated methylene group;
• and
• b) reacting the resulting anion with a fluoroalkyl halide of the formula R.sub.f C.sub.n H.sub.m X in a solvent comprising a mixture of tetrahydrofuran and n-methylpyrrolidinone to form the fluorinated ester compound.