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

Journal Article · Tue May 15 04:00:00 EDT 2018 · Russian Chemical Bulletin

DOI:https://doi.org/10.1007/S11172-018-2142-3· OSTI ID:22863344

Baichurin, R. I. ^[1]

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1. Herzen State Pedagogical University of Russia (Russian Federation)

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 Et{sub 3}N. When treated with 4-chlorothiophenol in the presence of Et{sub 3}N, 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, {sup 1}H and {sup 13}C{"1H} NMR spectroscopy using {sup 1}H–{sup 13}C HMQC, {sup 1}H–{sup 13}C, and {sup 1}H–{sup 15}N HMBC techniques. Methyl 2-[(4-methylphenyl)sulfanyl]-3-nitroacrylate exists as the Z-isomer, as confirmed by X-ray diffraction.

• OSTI ID: 22863344
• Journal Information: Russian Chemical Bulletin, Journal Name: Russian Chemical Bulletin Journal Issue: 5 Vol. 67; ISSN RCBUEY; ISSN 1066-5285
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ACRYLATES
CARBON 13
HYDROBROMIC ACID
HYDROGEN 1
ISOMERS
NITROGEN 15
NUCLEAR MAGNETIC RESONANCE
SPECTROSCOPY
SYNTHESIS
THIOPHENOLS
X-RAY DIFFRACTION