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Comparison of the electrophilic and free-radical addition of halogens with hexafluoro-1,3-butadiene and 1,3-butadiene
Ist Teil von
Journal of fluorine chemistry, 2003-10, Vol.123 (2), p.171-176
Ort / Verlag
Elsevier B.V
Erscheinungsjahr
2003
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Graphic
Ionic and photochemical reaction of chlorine (Cl
2), bromine (Br
2) and iodine monochloride (ICl) to hexafluoro-1,3-butadiene (
1) and 1,3-butadiene (
2) were carried out under conditions that would provide product distributions under controlled ionic or free-radical conditions. Product distributions for ionic reaction of Cl
2 and Br
2 with
1 are similar and suggest a weakly-bridged halonium ion species. Theoretical calculations support weakly-bridged chloronium and bromonium ions for both dienes
1 and
2. There are more of the 1,4-dihalo-2-butene products from ionic halogenation of
1 than
2 which correlates with the greater charge density on carbon-4 of halonium ions from
1. Ionic and free-radical reactions of ICl with
1 give 8 and 2% of 3-chloro-4-iodohexafluoro-1-butene and 4-chloro-3-iodohexafluoro-1-butene, respectively. The minor
cis-1,4-dihalo-2-butene products from
1 and
2 are reported when formed.