1964 Volume 12 Issue 12 Pages 1446-1451
The addition of cyanogen bromide to an acetylenic bond was studied. Phenylacetylene reacted with cyanogen bromide in the presence of aluminum bromide to afford trans-β-bromocinnamonitrile. Similarly, p-bromo-and p-methoxyphenylacetylene, tolane and methylphenylacetylene yielded corresponding β-bromocinnamonitriles. Nevertheless, p-nitrophenylacetylene did not react with cyanogen bromide under the same conditions.