Potential Antiradiation Compounds II. Extension of the Nitro-Thiolacetate Route

Thiolacetic acid was added to 3,4-methylenedioxy-ω-nitrostyrene to give 1-(3′,4′-methylenedioxyphenyl)-1-acetthio-2-nitroethane which was reduced with lithium aluminum hydride to produce 1-(3′,4′-methylenedioxyphenyl)-1-mercapto-2-aminoethane. Other substituted nitrostyrenes containing the 3,4-dimethoxy- and 3-methoxy-4-acetoxy groups also reacted with thiolacetic acid to give the corresponding addition products, but 3-acetoxy-4-methoxy-ω-nitrostyrene underwent an anomalous reaction with the formation of elemental sulfur. 1-Phenyl-2-nitro-1-propene added thiolacetic acid to give 1-phenyl-1-acetthio-2-nitropropane, but the latter compound was cleaved by lithium aluminum hydride to benzyl mercaptan and ethylamine.