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

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

Research outputpeer-review

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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Acrylates
Isomers
Nuclear magnetic resonance spectroscopy
X ray diffraction
thiophenol
vitamin B 12 factor III

Cite this

Makarenko, S. V. ; Baichurin, R. I. ; Gurzhiy, V. V. ; Baichurina, L. V. / Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates. In: Russian Chemical Bulletin. 2018 ; Vol. 67, No. 5. pp. 815-821.
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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.",
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Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates. / Makarenko, S. V.; Baichurin, R. I.; Gurzhiy, V. V.; Baichurina, L. V.

In: Russian Chemical Bulletin, Vol. 67, No. 5, 01.05.2018, p. 815-821.

Research outputpeer-review

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T1 - Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates

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AU - Baichurin, R. I.

AU - Gurzhiy, V. V.

AU - Baichurina, L. V.

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N2 - 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.

AB - 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.

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