Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates

Abstract

Alkyl 2-arylsulfanyl-3-nitroacrylates were synthesized by the conjugate Michael addition of thiophenols to alkyl 3-bromo-3-nitroacrylates followed by elimination of HBr on treatment with Et3N. When treated with 4-chlorothiophenol in the presence of Et3N, alkyl 2-[(4-chlorophenyl) sulfanyl]-3-nitroacrylates can be transformed into alkyl 2,3-bis[(4-chlorophenyl)sulfanyl]- acrylates. The structures of the synthesized compounds were characterized by IR, UV, 1H and 13C{1H} NMR spectroscopy using 1H–13C HMQC, 1H–13C, and 1H–15N HMBC techniques. Methyl 2-[(4-methylphenyl)sulfanyl]-3-nitroacrylate exists as the Z-isomer, as confirmed by X-ray diffraction.