Details

Autor(en) / Beteiligte

• Shellhamer, Dale F
• Gleason, David C
• Vaughan, G.Gawayne
• Ryan, Andrew J
• Titterington, Peter K
• Heasley, Victor L
• Lehman, Jeffrey J

Titel

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.