Alkyne zipper reaction
The alkyne zipper reaction is an organic reaction that involves isomerization of a non terminal alkyne into a terminal alkyne. This reaction was first reported by Alexey Favorsky in 1887 (J. Russ. Phys.-Chem. Soc., 19, 414 (1887)). Also, this reaction was reported by Charles Allen Brown and Ayako Yamashita in 1975.[1] The isomerization reaction proceeds for straight-chain alkynes and acetylinic alcohols. The conversion provides a useful approach for remote functionalization in long-chain alkynes.[2]
The reaction requires a
- HO–CH2C≡C–(CH2)6CH3 → HO(CH2)8–C≡CH
Mechanism
The alkyne zipper reaction requires a
The potassium 3-aminopropylamide deprotonates the less-substituted methylene adjacent to the alkyne group.[3][1]
The 3-aminopropylamine anion attacks the same lesser-substituted carbon adjacent to the
These steps will be repeated, essentially moving the
References
- ^ .
- ^ a b Suzanne R. Abrams and Angela C. Shaw (1988). "Triple Bond Isomerizations: 2- to 9-decyn-1-ol". Organic Syntheses. 66: 127; Collected Volumes, vol. 8, p. 146.
- ^ a b c d e "Alkyne Zipper Reaction". SynArchive. 2017. Archived from the original on December 22, 2017. Retrieved December 19, 2017.
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