Phenylacetylene is stereoselectively brominated by molecular bromine adsorbed on graphite in carbon tetrachloride, to produce E-α-β-dibromostyrene; isomerisation of the E-isomer to the Z-isomer, usually catalysed by bromine, is inhibited by graphite.
M. Kodomari, N. Tanaka, S. Yamamura and S. Yoshitomi, J. Chem. Soc., Chem. Commun., 1987, 1850 DOI: 10.1039/C39870001850
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