Synthesis and structure of alkyl-α-arylamino-β-bromo-β-nitroacrylates, new functionalized β-nitroenamines

Abstract

New bromonitroenamine compounds, alkyl-2-arylamino-3-bromo-3-nitroacrylates, were synthesized and characterized using IR, UV, 1H and 13C NMR spectroscopy, and X-ray analysis. Their molecules were found to have the E-configuration and to exist as highly conjugated structures. According to the X-ray analysis, in the ethyl-3-bromo-2-(p-bromophenylamino)-3-nitroacrylate molecule the bromonitroenamine moiety is almost planar, the ester group is located completely out of the C=C double bond plane, amino hydrogen and nitro oxygen atoms form an intramolecular hydrogen bond.