Cyclooctyne properties

On treatment with aqueous silver nitrate it forms a stable crystalline complex (78), from which 75 can be recovered almost quantitatively by addition of ammonia ". Anhydrous nickel(ii) bromide converts cyclooctyne into the trimer (79) with a quantitative yield . However, when the reaction was carried out in the presence of a trace of water, the dimeric cyclobutadiene-nickel bromide complex (80) was obtained in 9-4% yield, together with 79 (85%) . The spectroscopic properties of 80 showed close similarity with those of the tetramethylcyclobutadiene-nickel chloride complex . 

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