Pentafluorophenyl alkyl and vinyl ethers

Abstract

The sy nthes is or various derivatives or pe ntafluorophene tole of the type C.FsOCH,C H, R is described. The R group was c hlorin e, bromine, hydroxyl , pe ntafluoroph e noxy , acetoxy, and trifluoroacetoxy. 2-P e ntafluoroph e noxy-l ,1, I-triflu.o roethane and 1,I-bis(pentafluorophenoxy)e than e we re s imilarly sy nthes ized. A study was mad e of the behavior of these e thers toward pyrolysis, acids, and bases. In general, those e the rs co ntaining ,B-hydrogen atoms give pentafluorophenol on pyrolysis. Some compounds, such as 2-pentafluorophenoxyethyl bromide, give rea rranged products as well. Under basic co ndition s, cleavage to pentafluorophenol was observed with aqueous potassium hydroxide , whereas th e use of solid potass ium hydroxide pellets gives de hydrohalogenated produ cts. Conce ntrated s ulfuri c acid ca us es cleavage of most of th e e th e rs employed. 2-Pentatluorophenoxy-l,I,ItriAuoroethan e resists attack both by acids and bases.The sy nthes is and polym e rization or two new vinyl monomers, pe ntaAuorop he nyl vinyl ether and 1,2-difluorovinyl pentaAuorophenyl ether, are also presented.