Addition of chlorine,bromine and bromine chloride to some α,β-unsaturated methyl esters |
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Authors: | Ilpo OO Korhonen Maija Pitkänen Jorma NJ Korvola |
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Institution: | Department of Chemistry, University of Jyväskylä, SF-40100 Jyväskylä 10, Finland |
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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 (SN1 or SN2) is discussed with respect to the double bond substitution and regioisomer proportions. The dihalo products were identified by MS, 1H and 13C NMR. |
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