ADDITION OF CHLORINE, BROMINE AND BROMINE CHLORIDE TO SOME α,β-UNSATURATED METHYL ESTERS

Article abstract of DOI:10.1016/0040-4020(82)85011-4

The additions of chlorine, bromine and bromine chloride to trans methyl 2-butenoate 1, trans methyl 2-methyl-2-butenoate 2 and methyl 3-methyl-2-butenoate 3 under ionic conditions were studied.Bromine chloride addition always gave as a major regioisomer the 2-bromo-3-chloro compound, almost quantitatively in the case of 3.The mechanism of bromonium ion ring-opening (S_N1 or S_N2) is discussed with respect to the double bond substitution and regioisomer proportions.The dihalo products were identified by MS, 1H and 13C NMR.