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The reaction of terminal alkynes with hydrazines in the presence of TpRuCl(PPh 3 ) 2 (Tp = tris(pyrazolyl)borate) as a catalyst gave nitriles. This reaction involves the intermolecular attack of nitrogen nucleophiles at the α-carbon atom of (vinylidene)metal intermediates which are generated from terminal alkynes.
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Fukumoto et al. (2002) studied this question.
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