Electrophilic Addition of Halogenes and Hydrogen Halides to
1-Halogeno-3-buten-3-ynes

  1-Halogeno-3-buten-1-ynes add clorine and bromine mainly, at the doble bond.

  Addition of hydrogen bromide to 1-chloro-3-buten-1-yne and hydrogen iodide to all the 1-halogeno-3-buten-1-ynes leads to fixation of the proton at the first acetylenic carbon atom stereospecifically in the trans position to form cis-diene dihalides.

  In the reactions of all 1-halogeno-3-buten-1-ynes with hydrogen chloride and in the reactions of 1-bromo- and 1-iodo-3-buten-3-ynes with hydrogen bromide full or partial reduction of the halogen occurs.