The addition of SF5Br to acrylic esters: pathways to γ-SF5-propane derivatives

Reaction of SF5Br with various acrylic esters, CH2CHCOOR, where R = C2H5/C(CH3)3 and CH2C(CH3)COOCH3, CH2C(CH2Cl)-COOC2H5, CH2C(n-C7H15)COOC2H5 resulted in 1:1 adducts with the SF5-group attached to the CH2 portion of the acrylic ester. These adducts were converted to halogen-free saturated esters, an alcohol [SF5(CH2)3OH] an acid [SF5(CH2)2COOH] and a bromide [SF5(CH2)3Br]. Therefore, a method for chain-elongation of SF5-aliphatic hydrocarbons has been devised. With ethyl acrylate, a 2:1 adduct was also isolated. The reaction of SF5Cl with (C2H5O)2CCHCOOC2H5 gave chloromalonate. The compounds were characterized by their infrared, nuclear magnetic and mass spectral data.