The diphenylphosphide ion in liquid ammonia reacts with alk-2-ynyl halides by nucleophilic attack on bromine in some cases, and in others by nucleophilic attack on carbon.
W. Hewertson and I. C. Taylor, J. Chem. Soc. D, 1970, 119 DOI: 10.1039/C29700000119
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