Alkyne zipper reaction

The alkyne zipper reaction is a reaction which isomerizes an organic compound containing an internal alkyne into a terminal alkyne. This was first reported by Charles Allen Brown and Ayako Yamashita in 1975.

The reaction requires a strong base. The base used by Brown and Yamashita was the potassium salt of 1,3-diaminopropane. Ethylenediamine is not suitable as a replacement for 1,3-diaminopropane, and it gives unsatisfactory results.