A practical, convenient, and safe cyano(nitro)methylation method was developed, in which cyano-aci-nitroacetate served as a synthetic equivalent of anionic nitroacetonitrile (NAN). Cyano-aci-nitroacetate, which possesses three different functional groups on the same carbon, reacts with ketones and aldehydes to afford polyfunctionalized nitriles, such as glutaronitriles, α-nitro-α, β-unsaturated nitriles and α-nitro-δ-keto nitrile. Furthermore, the obtained nitrile products can be used as precursors of polyfunctionalized heterocyclic compounds.
A novel surfactant (C7-azo-C7) containing an azobenzene skeleton has been synthesized and stable oil in water (O/W)-type emulsions consisting of n-octane and water have been prepared. Ultraviolet (UV) light irradiation of the emulsions promotes the cis isomerization of trans C7-azo-C7 and leads to the coalescence of the oil (octane) droplets in the emulsions, that is, demulsification. In the course of the C7-azo-C7 synthesis, a synthetic intermediate has been found to form gold-colored crystals. It is found that the molecules produce J-aggregates in the crystals. Water molecules in the crystals will be essential for the formation of the stable J-aggregates and the resultant gold luster.