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Ionic and radical addition of chlorine, bromine and some halogen systems of butadiene monoxide (4)
Author(s) -
Shellhamer Dale F.,
Green Richard C.,
Luttrull Jeffrey K.,
Seneker Stephan D.,
Potter Mark K.,
Heasley Victor L.,
Heasley Gene E.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200147
Subject(s) - chemistry , bromine , chlorine , halogen , ionic bonding , halogenation , hypochlorite , photochemistry , medicinal chemistry , inorganic chemistry , organic chemistry , polymer chemistry , ion , alkyl
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.