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

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Abstract

Iodoperfluoroalkyl alcohols RFCH2CHI(CR2)nOH (RF= C6F13; R = H, CH3; n = 1-3, 9) have been readily prepared in high yield by the addition of perfluoroalkyl iodides RFI to allylic and other unsaturated alcohols at 120 °C in the presence of a catalytic amount (10% mol) of metallic copper powder. The dibenzoyl peroxide-induced reaction gave lower yields of the addition products in most cases. The chemical changes of iodoperfluoralkylated alcohols to epoxides and alcohols are described. A discussion of the by-products obtained and of the reaction mechanism is provided. © 1994.

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Kotora, M., Hácek, M., Ameduri, B., & Boutevin, B. (1994). Copper-catalyzed addition of perfluoroalkyl iodides to unsaturated alcohols and transformation of the addition products. Journal of Fluorine Chemistry, 68(1), 49–56. https://doi.org/10.1016/0022-1139(93)02993-O

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