Spectroscopic evidence for 1,2-diiminoethane – a key intermediate in imidazole synthesis

Abstract

extrusion at 3 K in solid argon and can be photochemically interconverted. In a matrix isolation pyrolysis experiment at 600 °C with 1,2-diazidoethane as the starting material we observe hydrogen cyanide and formaldimine as the main decomposition products. All experimental findings are supported by deuterium labeling experiments and B3LYP/6-311++G(2d,2p) calculations. Irradiation of 1,2-diazidoethane in aqueous solution leads to the formation of imidazoles as indicated by NMR spectroscopy and GC-MS analysis. Our results underline the key role of diimines as building blocks in N-heterocyclic chemistry.

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