Tetrahedron

Addition of chlorine, bromine and bromine chloride to some α, β-unsaturated methyl esters

IOO Korhonen, M Pitkänen, JNJ Korvola

Index: Korhonen, Ilpo O. O.; Pitkaenen, Maija; Korvola, Jorma N. J. Tetrahedron, 1982 , vol. 38, # 18 p. 2837 - 2841

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Citation Number: 7

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 ...

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