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.