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

S. V. Makarenko, R. I. Baichurin, V. V. Gurzhiy, L. V. Baichurina

Research output

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, H-1 and C-13{H-1} NMR spectroscopy using H-1-C-13 HMQC, H-1-C-13, and H-1-N-15 HMBC techniques. Methyl 2-[(4-methylphenyl)sulfanyl]-3-nitroacrylate exists as the Z-isomer, as confirmed by X-ray diffraction.

Original languageEnglish
Pages (from-to)815-821
Number of pages7
JournalRussian Chemical Bulletin
Volume67
Issue number5
DOIs
Publication statusPublished - 1 May 2018

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