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Issue 5, 1973
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Acetylene–allene isomerisations. Part II. Base catalysis by sodium amide in liquid ammonia

Abstract

Isomerisation of hex-1-, -2-, and -3-yne, and hexa-1,2- and -2,3-diene catalysed by sodium amide in liquid ammonia (concentrating on the first 20% or so of isomerisation of the pure compounds) is reported. The stepwise acetylene–allene isomerisation path is apparently followed. Differences in isomerisation caused by this catalyst and by potassiu t-butoxide in t-butyl alcohol are discussed. The importance of these results in view of the widely used reduction of alkynes to trans-alkenes by sodium in liquid ammonia is noted. Conjugated dienes were not formed during these isomerisations. The kinetic acidity of a proton attached to an allenic system is concluded to be greater than that of a proton conjugated to an allenic system.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1973, 672-676
Article type
Paper

Acetylene–allene isomerisations. Part II. Base catalysis by sodium amide in liquid ammonia

M. D. Carr, L. H. Gan and I. Reid, J. Chem. Soc., Perkin Trans. 2, 1973, 672
DOI: 10.1039/P29730000672

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