Alkyne zipper reaction

The alkyne zipper reaction is an organic reaction of unsaturated hydrocarbons. In the presence of an extremely strong base, a non-terminal alkyne isomerizes to a terminal alkynylide anion:

The reaction is an equilibrium reaction, and is driven by formation (and possibly precipitation) of the terminal anion. The conversion proceeds for straight-chain alkynes and acetylinic ethers, and provides remote functionalization in long chains.

Zipper isomerization was first reported by Alexey Favorsky in 1887.

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