Abstract

Abstract Cis- and trans-α,α′-Dimethylstilbene, heated with a little sulfuric acid at 210°, were isomerized to an equilibrium mixture consisting of 55% of the trans and 45% of the cis isomers. Heated with iodine at 210°, they yielded meso-2,3-diphenylbutane. The action of bromine produced 1,4-dibromo-2,3-diphenyl-2-butene; under certain experimental conditions the concurrent cis-trans isomerization was observed. This fact, together with the isolation of a small smount of α–bromoacetophenone as a by-product, supports the view that the reaction proceeds by a mechanism involving bromine atoms. The action of bromine on some α,α′-disubstituted stilbenes was examined. The reactions observed were discussed in terms of the steric effect exerted by the bulky groups at the ethylenic linkage.

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