Journal of the Chemical Society. Perkin transactions II p. 1714 - 1720 (1980)
Update date:2022-08-05
Topics:
Tanaka, Ryuichi
Zheng, Shi-Qin
Kawaguchi, Kenji
Tanaka, Takehide
Nucleophilic reactions between halogeno(phenyl)acetylenes and halide ions, ArC≡CX + Y-, where Ar = C6H5 or p-ClC 6H4, X = Cl or Br, and Y = Cl or Br, have been examined. Halogen exchange of the Finkelstein type was observed for the first time in acetylene halides in anhydrous dimethyl sulphoxide when X = Br and Y = Cl. This exchange did not occur with other X-Y combinations. In the presence of up to 20% water in dimethyl sulphoxide, or under aqueous-organic phase-transfer catalytic conditions, nucleophilic addition (formally of HY) took place for all the X-Y combinations studied. In the additions, the nucleophile Y- invariably attacked the carbon to which the phenyl group was bound. The mode of HY addition was stereospecifically trans; accordingly, the resulting dihalogenostyrenes always had the (Z)-1,2-dihalogeno-configuration.
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