Tetrahedron p. 4787 - 4792 (1985)
Update date:2022-08-11
Topics:
Schmid, George H.
Garratt, Dennis G.
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.
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