Kinetic study of the addition of trihalides to unsaturated compounds in ionic liquids. Evidence of a remarkable solvent effect in the reaction of ICl2-

The Journal of Organic Chemistry
Cinzia Chiappe, Daniela Pieraccini

Abstract

The kinetic constants and activation parameters for the reactions of Br(3)(-) and ICl(2)(-) with some alkenes and alkynes have been determined in the ionic liquids [bmim][PF(6)], [emim][Tf(2)N], [bmim][Tf(2)N], [hmim][TF(2)N], [bm(2)im][Tf(2)N], and [bpy][TF(2)N] (where emim = 1-ethyl-3-methylimidazolium, bmim = 1-butyl-3-methylimidazolium, hmim = 1-hexyl-3-methylimidazolium, bm(2)im = 1-butyl-2,3-dimethylimidazolium, bpy = butylpyridinium, PF(6) = hexafluorophosphate, and Tf(2)N = bis(trifluoromethylsulfonyl)imide) and in 1,2-dichloroethane. The rates of both reactions increase on going from 1,2-dichloroethane to ILs. Evidence suggests that, while the hydrogen bonding ability of the imidazolium cation is probably the main factor able to increase the rate of the addition of ICl(2)(-) to double and triple bonds, this property has no effect on the electrophilic addition of Br(3)(-) to alkenes and alkynes. Furthermore, in the case of the ICl(2)(-) reaction, the hydrogen bonding ability of ILs can be exploited to suppress the unwanted nucleophilic substitution reaction on the products by the Cl(-) anion.

References

Nov 25, 2000·Angewandte Chemie·P Wasserscheid, W Keim
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Citations

Apr 8, 2011·Chemical Reviews·Jason P Hallett, Tom Welton
Oct 19, 2006·Chemical Communications : Chem Comm·Jun MoJianliang Xiao
Sep 26, 2015·The Journal of Physical Chemistry. B·Marcela GazitúaRodrigo Ormazábal-Toledo
Jun 20, 2012·Carbohydrate Polymers·Martin GerickeThomas Heinze
Nov 9, 2007·Physical Chemistry Chemical Physics : PCCP·Kaoru NobuokaYuichi Ishikawa
Aug 23, 2005·Angewandte Chemie·Christian F WeberRudi van Eldik
Oct 17, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Aining YaoTaiwei Chu
Oct 4, 2013·Organic & Biomolecular Chemistry·Eden E L TannerJason B Harper
Mar 22, 2008·The Journal of Organic Chemistry·Francesca D'AnnaRenato Noto
May 5, 2010·The Journal of Organic Chemistry·Guido AngeliniGabriella Siani
Nov 17, 2009·The Journal of Organic Chemistry·Riccardo BiniBenedetta Parisi
Jun 22, 2010·The Journal of Organic Chemistry·Francesca D'AnnaRenato Noto
Nov 10, 2009·The Journal of Organic Chemistry·Rodrigo CristianoRichard G Weiss
Jan 12, 2010·Journal of Chemical Theory and Computation·Cinzia ChiappeChristian Silvio Pomelli
Jul 30, 2009·The Journal of Organic Chemistry·Guido AngeliniGabriella Siani
Nov 4, 2006·The Journal of Organic Chemistry·Lorna CrowhurstTom Welton
Sep 9, 2006·The Journal of Organic Chemistry·Shifang LiuJianliang Xiao

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