I. Korhonen, M. Pitkänen, J. Korvola
1982
Citations
0
Influential Citations
12
Citations
Journal
Tetrahedron
Abstract
Abstract 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 N 1 or S N 2) is discussed with respect to the double bond substitution and regioisomer proportions. The dihalo products were identified by MS, 1 H and 13 C NMR.