22480-49-5Relevant articles and documents
Ionic and Radical Addition of Chlorine, Bromine and Some Halogen Systems of Butadiene Monoxide
Shellhamer, Dale F.,Green, Richard C.,Luttrull, Jeffrey K.,Seneker, Stephan D.,Potter, Mark K.,et al.
, p. 229 - 232 (2007/10/02)
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 symmetrical halonium ion is formed in the ionic halogenation of 4.Free radical reaction of bromine, chlorine, or trichloramine to 4 does not give ring-opened products as one might expect for formation of an epoxy carbonyl intermediate.The mechanistic implications from these observations are discussed.