Ionic and radical addition of chlorine, bromine and some halogen systems of butadiene monoxide (4)

DF Shellhamer, RC Green, JK Luttrull…

Index: Shellhamer, Dale F.; Green, Richard C.; Luttrull, Jeffrey K.; Seneker, Stephan D.; Potter, Mark K.; et al. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 229 - 232

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Citation Number: 3

Abstract

Abstract Ionic reactions of bromine, chlorine, methyl hypochlorite or N-bromosuccinimide with butadiene monoxide (4) give only 1, 2-addition products. The Markownikoff (1-halo-2- methoxy-3, 4-epoxybutane) and anti-Markownikoff (2-halo-1-methoxy-3, 4-epoxybutane) product ratios for ionic reaction of methyl hypochlorite and N-bromosuccinimide in methanol with 4 are similar to those obtained with 1-hexene. These data indicate that a rather ...