Adamantyl iodide, silver

Alkynylation of adamantyl iodide has been performed in one-step procedure with silver(I) acetylides.143 The procedure is not applicable to substrates such as /-butyl iodide that can easily eliminate HI. 

An investigation of the reactions of various silver acetylides with adamantyl bromide or iodide in several solvents showed that Sn products could be formed in low to satisfactory yields.120 Because adamantane is one of the products, the reaction may occur by an SrnI rather than an 5 1 mechanism. 

Silver trinitromethane undergoes addition to adamantyl (Ad) halides,31 methyl iodide, and trinitromethyl iodide (Scheme 1.7).32... 

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