84452-23-3Relevant articles and documents
β,γ-ACETYLENIC α-HYDROXY NITRILES. SYNTHESIS AND TRANSFORMATIONS IN ACIDIC AND ALKALI MEDIA
Bol'shedvorskaya, R. L.,Pavlova, G. A.,Filippova, T. M.,Vereshchagin, L. I.
, p. 1806 - 1809 (2007/10/02)
The synthesis of alkyl- and aryl-substituted acetylenic α-hydroxy nitriles was realized.Under alkaline conditions α-hydroxynitriles of the β,γ-acetylenic series undergo cyanohydrin decomposition into the initial acetylenic aldehyde and hydrogen cyanide.Alkaline cleavage in the presence of active manganese dioxide is accompanied by the formation of the intermediate unstable β,γ-ethynyl-α-keto nitrile with subsequent conversion into phenylacetylene and phenylpropiolic acid.In a weakly alkaline aqueous medium the β,γ-ethynyl-α-hydroxynitriles undergo isomerization to β,γ-vinyl-α-keto nitriles with subsequent substitution of the cyanide ion by a hydroxyl group.Under acidic conditions the β,γ-acetylenic α-hydroxy nitriles give acetylenic acids.
