Allenes. Part XX. The preparation of 3-alkyl- and 3,3-dialkylallenenitriles

Abstract

3-Alkyl- and 3,3-dialkylallenecarbonitriles are conveniently prepared in good yield from 1-alkyl and 1,1-dialkyl-3-bromoallenes by the action of cuprous cyanide in NN-dimethylformamide at 35–60° for 2 hours. Tertiary acetylenic alcohols may be directly converted into 3,3-dialkylallenecarbonitriles by stirring for 3 days with potassium cyanide, cuprous cyanide, and hydrobromic acid. The same mixture with a large excess of concentrated hydrochloric acid gives nearly equal quantities of chloro- and cyano-allenes.