Reaction of Nitrostyrenes and 1-Nitrohexane with Sodium Polysulfides and Sodium Hydroxide

Article abstract of DOI:10.1246/bcsj.55.625

The reaction of β-nitrostyrene with NaOH in refluxing EtOH-H2O (1:2) gives benzaldehyde, benzyl alcohol, benzoic acid, phenylacetic acid, β-phenylethyl alcohol, and polymeric materials.On the other hand, the reaction of β-nitrostyrene with Na2S4-NaOH in the same solvent gave acetophenone besides the same products obtained with NaOH.Acetophenone was likewise detected in the Na2S-NaOH and Na2S2-NaOH reactions. 4-Nitrostyrene was also allowed to react with Na2S4-NaOH in EtOH-H2O (4:1) to give a small amount of 4-aminoacetophenone.The formation of acetophenones suggests the occurrence of the Michael addition of polysulfide ion and supports our mechanism proposed previously for the reaction of p-nitrotoluene with Na2S4.The reaction of 1-nitrohexane with Na2S4-NaOH, in which the Michael addition is not conceivable, gives the same products as the reaction with NaOH.