The addition of free radicals to unsaturated systems. Part XVI. A reinvestigation of radical addition to 1,1,3,3,3-pentafluoropropene

Abstract

Photochemical reaction of trifluoroiodomethane with 1,1,3,3,3-pentafluoropropene gives the 1 : 1-adducts 1,1,1,3,3-pentafluoro-3-iodo-2-trifluoromethylpropane and 1,1,1,2,2,4,4,4-octafluoro-3-iodobutane in 75–85% yield and in a 60 : 40 ratio. A thermal reaction gives the isomeric 1 : 1-adducts as the major components but by-product formation increases. Photochemical reaction of hydrogen bromide with the olefin is not very reproducible, but gives the 1 : 1-adducts 1-bromo-1,1,3,3,3-pentafluoropropane and 2-bromo-1,1,1,3,3-pentafluoropropane, and 1,2-dibromo-1,1,3,3,3-pentafluoropropane as the main products.