Ionic reactions of halogens with 4-halo-1,1,2-trifluorobut-1-enes

CHED 598

Matthew P. Herrick, dshellha@ptloma.edu, Rachel N. Jones, Ryan J. Weiss, rweiss@pointloma.edu, and Dale F. Shellhamer, dshellha@ptloma.edu. Department of Chemistry, Point Loma Nazarene University, 3900 Lomaland dr, San Diego, CA 92106
Reactions of chlorine and bromine (Cl2, Br2) with 4-Halo-1,1,2-trifluorobut-1-enes1 to form the 4- Halo-1,2,-dihalo-1,1,2,-trifluorobutane products are reported. Products form from ring-opened halonium ion intermediates2. In some cases, the neighboring number 4 halogen groups participate with the three-membered intermediates in the formation of five-membered tetramethylene halonium ions3. The five-membered tetramethylene halonium ions can open to give rearranged products, in which the number 4 halogen group is exchanged with the number 1 halogen. Formation of the rearranged products depends on the nucleophilicity of the number 4 group as well as the charge distribution on the number 1 carbon of the three member ring halonium ions.