Silver(I) acetylides facilitate direct carbon–carbon bond formation at the bridgehead position of adamantane, and in some instances related systems such as carborate anions and bicyclo[2.2.2]octanes. Substrate constraints along with attempts to further understand the underlying mechanism are presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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