22480-49-5Relevant academic research and scientific papers
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.
