The preparation and reactions of some carbinols containing the pentafluoropropenyl group - Tarrant, P.; Whitfield, R.W.; Summerville, R.H. (Elsevier)
1,1,1,2,3,3-Hexafluoropropane was dehydrofluorinated to yield a 1:1 mixture of (Z)- and (E)-1H-pentafluoropropene. This mixture was found to react with butyl-lithium to give pentafluoropropenyl-lithium, which reacted with a series of carbonyl compounds to give exclusively (Z)- pentafluoropropenyl carbinols. The yields were greater than 50%, indicating that the lithium reagent does not retain its stereochemical identity at low temperature, contrary to the hydrocarbon analog. Hydrolysis of the CF"3CFCFLi also gives exclusively the (Z)-F-olefin. Treating (Z)-CF"3CFCFC(CF"3)"2OH with SF"4 gave the (E) isomer. Some chemical properties of the carbinols are described.
http://linkinghub.elsevier.com/retrieve/pii/S0022-1139(00)82531-2
Keywords: V