Adamantyl bromide, silver

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. 

The carbene units can directly be fused to the phenyl ring by reacting 2-phenyl-1,3,4-oxa-diazole with p- or m-phenylenediamine dihydrochloride in o-dichlorobenzene [348,349]. Quartemisation with adamantyl bromide and genesis of the carbene with BuTlK or NaH follows standard procedures [350], The CuX (X = Cl, 1) complexes of this bis-carbene ligand have similar strucmres to the silver(I) complexes seen in Figure 3.109. 

Methods of Synthesis.— The salt method, involving the alkylation of a sulphide with an alkyl halide followed by removal of an oc-proton with an appropriate base, continues to be of wide applicability, even for complex structures. Adamantyl bromide and methyl ethyl sulphide were smoothly converted into the salt using silver tetrafluoroborate. l-Iodo-3-chloropro-pane alkylated diphenyl sulphide with silver tetrafluoroborate assistance,... 

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