Reaction of halogens and interhalogens with 4-halo-1,1,2-trifluorobut-1-enes

CHED 429

Rachel N Jones, Ryan J. Weiss, rweiss@pointloma.edu, and Dale F. Shellhamer, dshellham@ptloma.edu. Department of Chemistry, Point Loma Nazarene University, 3900 Lomaland Dr, San Diego, CA 92106
Reactions of halogens chlorine (Cl2), bromine (Br2), and interhalogens iodine monochloride (ICl) or iodine monobromide (IBr) with 4-Halo-1,1,2-trifluorobut-1-enes were studied. Ionic reactions of halogen electrophiles give three-membered halonium ion intermediates (1) that can rearrange by neighboring group participation from the 4-Halosubstituent to a five-membered ring trifluorotetramethylene halonium ions (2). The effect that the number-4-halogen substituent (Z=Cl, Br or I) has on formation of 2 (X=Cl, Br or I) is presented.