The free radical addition of Cl(CF~2)~nI (n=2,4,6,8) 1a to allylic compounds (CH~2=CH--CH~2X, X=OH, OAc) and vinyl acetate in the presence of initiator gave the corresponding adducts Cl(CF~2)~nCH~2CHICH~2OH (2a～d), Cl(CF~2)~nCH2 CHICH~2OAC (3a～d) and Cl(CF~2)~nCH~2CHIOAc (4a～d) with good yields. The deiodination of 2a～d to Cl(CF~2)~nCH~2CH~2 CH~2OH (5a～d) by LiAlH~4 went smoothly. The alcohol Cl(CF~2)~nCH=CHCH~2OH 6a～c was formed from the reaction of 2a～d with KOH-methanol, however, the epoxide was obtained with aqueous NaOH. Zinc reduction of 2a～d and 3a～d in isopropanol in the presence of small amounts of acetic acid affoeded the elimination products Cl(CF~2)~n- CH~2CH=CH~2(8a～d). Contrarily the reduction of 4a～d with Zinc, followed by hydrolysis with KOH-methanol-water gave clearly Cl(CF~2)~n(CH~2)~2OH(10a～d).

Key words: EPOXIDE, ALCOHOL, ADDITION REACTION