Copper-catalyzed addition of perfluoroalkyl iodides to unsaturated alcohols and transformation of the addition products

Article abstract of DOI:10.1016/0022-1139(93)02993-O

Iodoperfluoroalkyl alcohols R_FCH2CHI(CR2)nOH (R_F = C6F13; R = H, CH3; n = 1-3, 9) have been readily prepared in high yield by the addition of perfluoroalkyl iodides R_FI to allylic and other unsaturated alcohols at 120 deg C in the presence of a catalytic amount (10percent mol) of metallic copper powder.The dibenzoyl peroxide-induced reaction gave lower yields of the addition products in most cases.The chemical changes of iodoperfluoroalkylated alcohols to epoxides and alcohols are described.A discussion of the by-products obtained and of the reaction mechanism is provided.