Addition to 2, 4-dienes. Halogenation of ethyl sorbate

DF Shellhamer, VL Heasley, JE Foster…

Index: Shellhamer,D.F. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 12 p. 2141 - 2145

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Citation Number: 13

Abstract

The addition of chlorine and bromine to ethyl sorbate (la) gave 1, 2-and 1, a-dihalo products derived from attack of the halogen across the y, 6 double bond. Chlorination of la under ionic conditions proceeds through a tightly bridged chloronium ion intermediate, as indicated by the stereospecific formation of erythro-1, 2-dichloride 3a. Stereospecificity in 3a is lost when chlorine is added to la under radical conditions, indicating a molecule-induced homolysis ...