Stereochemistry of chlorination and chloroiodination of alkylphenylacetylenes by CuCl2

Abstract
Reaction of alkylphenylacetylenes, PhCCR (R = H or alkyl)(1), with CuCl2–LiCl or CuCl2–I2 in acetonitrile gives the corresponding dihalogenoalkenes in good yields; E-addition is favoured except in the chlorination of (1, R = But) where Z-addition predominates.

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