Cyclohexyne is an organic compound with the formula . It strained cyclic alkyne. Due to its high ring strain, cyclohexyne cannot be isolated but exists only as a short-lived reactive intermediate.
Synthesis Cyclohexyne can be generated by the elimination of hydrogen halides from suitable precursors. Other methods include the use of organolithium reagents or photolytic or thermal activation of precursor molecules.
Cyclohexyne as a ligand A platinum complex of cyclohexyne can be prepared by elimination from 1-bromocyclohexene with lithium diisopropylamide in the presence of tris(triphenylphosphine)platinum(0). An alternative synthetic method is the reduction of 1,2-dibromocyclohexene with sodium amalgam in the presence of tris(triphenylphosphine)platinum(0). Such a complex can also be prepared by trapping with tris(triphenylphosphine)platinum(0) when cyclohexenylphenyliodonium tetrafluoroborate is used as the starting material for cyclohexyne.
Another complex, in this case with zirconium, can be prepared by treating methylzirconocene chloride cyclohexenyllithium followed by trimethylphosphine.
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