Alkyne zipper reaction

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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.[1]

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.[2]

[edit] References

  1. ^ C. A. Brown and A. Yamashita (1975). "Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide". J. Am. Chem. Soc. 97 (4): 891–892. doi:10.1021/ja00837a034. 
  2. ^ Suzanne R. Abrams and Angela C. Shaw (1988). "Triple Bond Isomerizations: 2- to 9-decyn-1-ol". Org. Synth. 66: 127; Coll. Vol. 8: 146. 
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