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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.

в: Russian Chemical Bulletin, Том 67, № 5, 01.05.2018, стр. 815-821.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Makarenko, SV, Baichurin, RI, Gurzhiy, VV & Baichurina, LV 2018, 'Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates', Russian Chemical Bulletin, Том. 67, № 5, стр. 815-821. https://doi.org/10.1007/s11172-018-2142-3

APA

Makarenko, S. V., Baichurin, R. I., Gurzhiy, V. V., & Baichurina, L. V. (2018). Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates. Russian Chemical Bulletin, 67(5), 815-821. https://doi.org/10.1007/s11172-018-2142-3

Vancouver

Makarenko SV, Baichurin RI, Gurzhiy VV, Baichurina LV. Synthesis and structure of alkyl 2-arylsulfanyl-3-nitroacrylates. Russian Chemical Bulletin. 2018 Май 1;67(5):815-821. https://doi.org/10.1007/s11172-018-2142-3

Author

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

BibTeX

@article{847989c8ee414d81bd58f03abd6132e0,
title = "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, 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.",
keywords = "BETA-PHENYLTHIO, C-13, H-1, Michael reaction, N-15, NITRO OLEFINS, NITROETHYLENE, NMR, STEREOCHEMISTRY, X-ray diffraction, Z-isomers, nitroacrylates, nitroalkenes, sulfanylacrylates, thiophenols",
author = "Makarenko, {S. V.} and Baichurin, {R. I.} and Gurzhiy, {V. V.} and Baichurina, {L. V.}",
year = "2018",
month = may,
day = "1",
doi = "10.1007/s11172-018-2142-3",
language = "English",
volume = "67",
pages = "815--821",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer Nature",
number = "5",

}

RIS

TY - JOUR

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

AU - Makarenko, S. V.

AU - Baichurin, R. I.

AU - Gurzhiy, V. V.

AU - Baichurina, L. V.

PY - 2018/5/1

Y1 - 2018/5/1

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.

KW - BETA-PHENYLTHIO

KW - C-13

KW - H-1

KW - Michael reaction

KW - N-15

KW - NITRO OLEFINS

KW - NITROETHYLENE

KW - NMR

KW - STEREOCHEMISTRY

KW - X-ray diffraction

KW - Z-isomers

KW - nitroacrylates

KW - nitroalkenes

KW - sulfanylacrylates

KW - thiophenols

UR - http://www.scopus.com/inward/record.url?scp=85051849778&partnerID=8YFLogxK

U2 - 10.1007/s11172-018-2142-3

DO - 10.1007/s11172-018-2142-3

M3 - Article

AN - SCOPUS:85051849778

VL - 67

SP - 815

EP - 821

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 5

ER -

ID: 32835690