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Palladium-catalyzed dimerizations of alkynes are known but since the presence of o-tolyl zinc chloride would result in deprotonation of the alkyne formed in situ, it is believed that 52 is formed by a different mechanism. See: (a) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591.
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Palladium-catalyzed dimerizations of alkynes are known but since the presence of o-tolyl zinc chloride would result in deprotonation of the alkyne formed in situ, it is believed that 52 is formed by a different mechanism. See: (a) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591.
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The fact that (adamantylethynyl)zinc(II) chloride transmetalates faster than o-tolyl zinc chloride was confirmed by increasing the steric bulk on the organozinc reagent to the m-xylene derivative, resulting in sole formation of the byproduct 52.
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The fact that (adamantylethynyl)zinc(II) chloride transmetalates faster than o-tolyl zinc chloride was confirmed by increasing the steric bulk on the organozinc reagent to the m-xylene derivative, resulting in sole formation of the byproduct 52.
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