Fluoro-olefin chemistry. Part X. Some additions to 1-fluoropropene under ionic and free-radical conditions

Abstract

The reactions of bromine with cis- or trans-1-fluoropropene under ionic conditions result in stereospecific anti-additions, and the addition of hydrogen bromide gives 1-bromo-1-fluoropropane exclusively. Photoreaction of hydrogen bromide with the olefin affords hydrogen, the 1 : 1 adducts, MeCH₂·CHFBr and MeCHBr·CH₂F, in the ratio 90 : 10, and the olefin dibromide. Similarly photoreaction of trifluoroiodomethane with the olefin also results in bidirectional addition and the adducts, CF₃·CHMe·CHFl and MeCHl·CHF·CF₃, are formed in the ratio 49 : 51; under thermal conditions the adduct ratio is 46 : 54. The photoreaction of methanethiol with the olefin gives hydrogen, dimethyl disulphide, and 1,1-bis(methylthio)propane; 1 : 1 adducts were not detected in the products.