The reaction of chloro(phenyl)ethyne (1) with sodium azide in dimethyl sulphoxide gave the nucleophilic addition product (Z)-α-azido-β-chlorostyrene; phenylethynylnitrane (7) was trapped by the solvent to give N-(phenylethynyl)-S,S-dimethylsulphoximine (4), indicating the prior formation of the hitherto unknown substitution product azido(phenyl)ethyne (6).
R. Tanaka and K. Yamabe, J. Chem. Soc., Chem. Commun., 1983, 329 DOI: 10.1039/C39830000329
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