Alkyne zipper reaction

What is alkyne zipper reaction?

The alkyne zipper reaction, also known as the Brown alkyne zipper reaction or alkyne isomerization reaction or alkyne-allene rearrangement, is a chemical process that involves the isomerization of internal alkynes into terminal alkynes by treating them with potasium 3-aminopropylamide (KAPA) or lithium 3-aminopropylamide (LiAPA) (see list of acronyms).

alkyne zipper reaction - Brown alkyne zipper reaction - alkyne isomerization reaction
Alkyne zipper reaction


The alkyne zipper reaction was initially mentioned by A. Favorsky (Favorskii) in 1888. However, the specific variation presented here was likely first described in 1975.