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. [cite journal | author = C. A. Brown and A. Yamashita | title = Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide | year = 1975 | journal = J. Am. Chem. Soc. | volume = 97 | issue = 4 | pages = 891–892 | doi = 10.1021/ja00837a034 ]

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. [OrgSynth | author = Suzanne R. Abrams and Angela C. Shaw | title = Triple Bond Isomerizations: 2- to 9-decyn-1-ol | year = 1988 | volume = 66 | pages = 127 | collvol = 8 | collvolpages = 146 | prep = cv8p0146]

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