87261-45-8Relevant academic research and scientific papers
Regio- and stereospecific iodochlorination of alkenes and alkynes with polystyrene-[4-vinylpridinium dichloroiodate(I)]
Ket, Boris,Zupet, Pavel,Zupan, Marko
, p. 2503 - 2510 (2007/10/02)
Polystyrene-[4-vinylpyridinium dichloroiodate(I)] can be used for regio- and stereospecific iodochlorination of different alkenes and phenylsubstituted alkynes. In all cases the reaction followed the Markownikov type of regioselectivity and the addition p
Evidence for molecular complexes in the mechanism of additions of iodine monochloride to alkenes
Schmid, George H.,Gordon, James W.
, p. 2526 - 2534 (2007/10/02)
Immediately upon mixing ICl and 2,3-dimethyl-2-butene in CCl4 at 25 deg C a new absorption band due to an alkene - ICl molecular complex appears at 295 +/- 5 nm and decreases rapidly with time.The rate law under conditions of (alkene)0 >> (ICl)0/dt = kexpt(alkene)(ICl)3/AD(alkene)>3 where KAD is the equilibrium constant for the formation of a 1:1 alkene - ICl molecular complex.The addition of ICl to the Z and E isomers of 2-butene and 1-phenylpropene occurs by anti-stereospecific addition.The negative enthalpy of activation for the addition of ICl to 2,3-dimethyl-2-butene is evidence that one or more complexes are involved on the reaction coordinate prior to the rate-determining step.On the basis of analysis of the enthalpy changes during the reaction, it is proposed that both a 1:1 and a 1:2 alkene - ICl molecular complex is involved in the mechanism prior to the rate-determining step.
Involvement of Neighboring Chlorine in the Exchange Reactions of Iodine Monochloride and Vicinal Organic Iodochlorides
Schmid, George H.,Gordon, James W.
, p. 4010 - 4013 (2007/10/02)
The reaction of vicinal organic iodochlorides and ICl in CCl4 at 25 deg C forms vicinal organic dichlorides and iodine.The rate law for this exchange reaction of ICl and 2-chloro-3-iodo-2,3-dimethylbutane is overall third order: second order in ICl and first order in iodochloride with a value of k3 = 7.2 +/- 0.9 M-2s-1.Stereospecific exchange occurs in the reaction ICl and erythro- and threo-2-chloro-3-iodobutane.Thus the erythro isomer forms only meso-2,3-dichlorobutane while the threo isomers form only the dl dichloride.Nonstereospecific exchange occurs in the reaction of ICl and erythro- and threo-1-chloro-2-iodo-1-phenylpropane.The data support a mechanism involving a cationic intermediate.In addition, the chlorine atom is involved in the reaction prior to the product-determining step.
