Separation and interconversion of 3-amino-2-cyanoacrylates by high-performance liquid chromatography

Abstract High-performance liquid chromatography (HPLC) is the preferred method for the resolution of Z/E isomers. The partly known interconversion of the Z/E isomers of methy and ethyl 3-substituted amino-2-cyanoacrylates and amides was observed and quantitatively followed by HPLC analysis. In a solution of alkaline pH and containing methanol instead of acetonitrile, the interconversion is faster. The use of gas chromatography for the analysis of the isomers for unsubstituted aminocyanoacrylates was impracticable owing to the easy interconversion in the sample chamber.