Reaction to Halogens and Interhalogens with 4-Halo-1,1,2-trifluorobut-1-enes: Rearrangement of 3-Membered Halonium to 5-Membered Trifluorotetramethylene Halonium Ion Intermediates and Comparison of Open-Chloronium Fluorosubstituted Ions to Flurocarbocations from Protons (Preprint)

In this paper we investigate the influence that a 4-halosubstituent has on formation of three-membered halonium ions and their rearrangement to five-membered ring intermediates when chloronium, bromonium and iodonium ions from alkenes 1, 2 and 3 are formed in aprotic solvent (Scheme 1). We also compare the open-ion chloronium ions with the open-carbocations from addition of a proton to terminal fluorosubstituted alkenes. Sponsored in part by National Science Foundation Grants nos. CHE-0345551, CHE-0640547, and CHE-0417731. Prepared in collaboration with the Department of Chemistry, Point Loma Nazarene University, San Diego, CA. For publication in Inorganic Chemistry.