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Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates. / Zhelonkina, Yuliya V.; Khoroshilova, Olesya V.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Pelipko, Vasilii V.; Makarenko, Sergey V.; Vasilyev, Aleksander V.

In: ChemistrySelect, Vol. 8, No. 39, e2021302205, 18.10.2023.

Research output: Contribution to journal › Article › peer-review

Harvard

Zhelonkina, YV, Khoroshilova, OV, Ivanov, AY, Boyarskaya, IA, Pelipko, VV, Makarenko, SV & Vasilyev, AV 2023, 'Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates', ChemistrySelect, vol. 8, no. 39, e2021302205. https://doi.org/10.1002/slct.202302205, https://doi.org/10.1002/slct.202302205

APA

Zhelonkina, Y. V., Khoroshilova, O. V., Ivanov, A. Y., Boyarskaya, I. A., Pelipko, V. V., Makarenko, S. V., & Vasilyev, A. V. (2023). Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates. ChemistrySelect, 8(39), [e2021302205]. https://doi.org/10.1002/slct.202302205, https://doi.org/10.1002/slct.202302205

Vancouver

Zhelonkina YV, Khoroshilova OV, Ivanov AY, Boyarskaya IA, Pelipko VV, Makarenko SV et al. Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates. ChemistrySelect. 2023 Oct 18;8(39). e2021302205. https://doi.org/10.1002/slct.202302205, https://doi.org/10.1002/slct.202302205

Author

Zhelonkina, Yuliya V. ; Khoroshilova, Olesya V. ; Ivanov, Alexander Yu. ; Boyarskaya, Irina A. ; Pelipko, Vasilii V. ; Makarenko, Sergey V. ; Vasilyev, Aleksander V. / Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates. In: ChemistrySelect. 2023 ; Vol. 8, No. 39.

BibTeX

@article{74c373bfea124c48b9a4a6e718b02bb1,
title = "Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates",
abstract = "Methyl or ethyl 3-nitropropenoates (β-nitroacrylates) AlkO(O)C1−C2H=C3H−NO2 in reaction with arenes ArH in triflic acid CF3SO3H (TfOH) at room temperature in 1 h give rise to oximes of alkyl 2,3-diaryl-3-oxopropanoates AlkO(O)C−CH(Ar)−C(Ar)=NOH in yields of 42–92 %. The obtained oximes bearing ortho-methyl substituents in the aryl ring exist as atropoisomers in solutions. The study of protonated forms of β-nitroacrylates by NMR and DFT calculations has revealed that the reactive electrophiles are species AlkO(HO+)C1−C2H=C3H−N+(O)(OH) protosolvated on the acceptor groups NO2 and CO2R. Plausible reaction mechanism is based on the primary interaction of aromatic nucleophiles with these electrophilic species onto their carbon C2.",
keywords = "atropoisomers, cations, nitroacrylates, oximes, triflic acid",
author = "Zhelonkina, {Yuliya V.} and Khoroshilova, {Olesya V.} and Ivanov, {Alexander Yu.} and Boyarskaya, {Irina A.} and Pelipko, {Vasilii V.} and Makarenko, {Sergey V.} and Vasilyev, {Aleksander V.}",
note = "Zhelonkina Yu.V., Khoroshilova O.V., Ivanov A.Yu., Boyarskaya I.A., Pelipko V.V., Makarenko S.V., Vasilyev A.V. Reactions of alkyl β-nitroacrylates with arenes in triflic acid: synthesis of oximes of alkyl 2,3-diaryl-3-oxopropanoates. ChemistrySelect. 2023, V. 8, N. 39, e2021302205.",
year = "2023",
month = oct,
day = "18",
doi = "10.1002/slct.202302205",
language = "English",
volume = "8",
journal = "ChemistrySelect",
issn = "2365-6549",
publisher = "Wiley-Blackwell",
number = "39",

}

RIS

TY - JOUR

T1 - Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates

AU - Zhelonkina, Yuliya V.

AU - Khoroshilova, Olesya V.

AU - Ivanov, Alexander Yu.

AU - Boyarskaya, Irina A.

AU - Pelipko, Vasilii V.

AU - Makarenko, Sergey V.

AU - Vasilyev, Aleksander V.

N1 - Zhelonkina Yu.V., Khoroshilova O.V., Ivanov A.Yu., Boyarskaya I.A., Pelipko V.V., Makarenko S.V., Vasilyev A.V. Reactions of alkyl β-nitroacrylates with arenes in triflic acid: synthesis of oximes of alkyl 2,3-diaryl-3-oxopropanoates. ChemistrySelect. 2023, V. 8, N. 39, e2021302205.

PY - 2023/10/18

Y1 - 2023/10/18

N2 - Methyl or ethyl 3-nitropropenoates (β-nitroacrylates) AlkO(O)C1−C2H=C3H−NO2 in reaction with arenes ArH in triflic acid CF3SO3H (TfOH) at room temperature in 1 h give rise to oximes of alkyl 2,3-diaryl-3-oxopropanoates AlkO(O)C−CH(Ar)−C(Ar)=NOH in yields of 42–92 %. The obtained oximes bearing ortho-methyl substituents in the aryl ring exist as atropoisomers in solutions. The study of protonated forms of β-nitroacrylates by NMR and DFT calculations has revealed that the reactive electrophiles are species AlkO(HO+)C1−C2H=C3H−N+(O)(OH) protosolvated on the acceptor groups NO2 and CO2R. Plausible reaction mechanism is based on the primary interaction of aromatic nucleophiles with these electrophilic species onto their carbon C2.

AB - Methyl or ethyl 3-nitropropenoates (β-nitroacrylates) AlkO(O)C1−C2H=C3H−NO2 in reaction with arenes ArH in triflic acid CF3SO3H (TfOH) at room temperature in 1 h give rise to oximes of alkyl 2,3-diaryl-3-oxopropanoates AlkO(O)C−CH(Ar)−C(Ar)=NOH in yields of 42–92 %. The obtained oximes bearing ortho-methyl substituents in the aryl ring exist as atropoisomers in solutions. The study of protonated forms of β-nitroacrylates by NMR and DFT calculations has revealed that the reactive electrophiles are species AlkO(HO+)C1−C2H=C3H−N+(O)(OH) protosolvated on the acceptor groups NO2 and CO2R. Plausible reaction mechanism is based on the primary interaction of aromatic nucleophiles with these electrophilic species onto their carbon C2.

KW - atropoisomers

KW - cations

KW - nitroacrylates

KW - oximes

KW - triflic acid

UR - https://www.mendeley.com/catalogue/79d72a39-d2e0-3ad1-a993-05caa83ce543/

U2 - 10.1002/slct.202302205

DO - 10.1002/slct.202302205

M3 - Article

VL - 8

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 39

M1 - e2021302205

ER -

ID: 113744706