cas 2211-67-8, (±)-2,3-Dichlorobutane | Articles data

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NUCLEOPHILIC DISPLACEMENT REACTIONS AT Se(II). REACTION OF ARENESELENENYL CHLORIDES AND 2-CHLOROALKYL PHENYL SELENIDES
The products of the title reaction depend upon the relative concentrations of reactants.With equimolar concentrations or an excess of 2-chloroalkyl phenyl selenide, the products are 1,2-dichloroethane and a diaryldiselenide.When excess areneselenenyl chloride is used, the products are a diaryl diselenide and 2-chloroalkyl phenyl selenide dichloride.A mechanism involving nucleophilic displacement at selenenyl selenium is proposed to account for the observed products.Structural changes in the selenide on varying substituents in the 4-position of areneselenenyl chloride has little effect on the rate of the reaction.In the proposed continuum of mechanisms of nucleophilic displacement reactions at Se(II), an SN2-like transition state best accounts for the data.
Schmid, George H.,Garratt, Dennis G.
p. 4787 - 4792
(2007/10/02)

Involvement of Neighboring Chlorine in the Exchange Reactions of Iodine Monochloride and Vicinal Organic Iodochlorides
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.
Schmid, George H.,Gordon, James W.
p. 4010 - 4013
(2007/10/02)