SYNTHESIS AND POLYMERIZATION OF FLUORINATED MONOMERS BEARING A REACTIVE LATERAL GROUP

The synthesis of various omega-perfluorovinyl synthons, especially 1,1 ,2-trifluoro-1,4-pentadiene I (F2C=CFCH2CH=CH2) is described. These pr oducts were prepared according to a three-step scheme via the photoche mical addition of iodine monochloride to chlorotrifluotoethylene (CTFE ) leading to ICF2CFCl2/ICFClCF2Cl isomers, the relative amount of whic h depending on the way of initiation. Their reaction with allyl acetat e under radical conditions gave at least four isomers from the expecte d or rearranged compounds ClCF2CFClCH2CHXCH2Y or Cl2CFCF2CH2CHXCH2Y (w ith X, Y = I or OAc groups), the dechlorination and/or 'deiodoacetatis ation' of which produced 1 and various 4,3,5,5,5-perhalogenopentanes a s by-products. An optimization of the synthesis of 1 is proposed. All the compounds were characterized by H-1 and F-19 NMR. (C) 1998 Elsevie r Science S.A. All rights reserved.