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Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids : Experimental and Theoretical Study of Intermediate Cationic Species. / Borisova, Marina A.; Ryabukhin, Dmitry S.; Yu. Ivanov, Alexander; Boyarskaya, Irina A.; Shabalin, Dmitrii A.; Zelenkov, Lev E.; Yu. Schmidt, Elena; Trofimov, Boris A.; Vasilyev, Aleksander V.

In: European Journal of Organic Chemistry, Vol. 2022, No. 30, e202200468, 12.08.2022.

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

Harvard

Borisova, MA, Ryabukhin, DS, Yu. Ivanov, A, Boyarskaya, IA, Shabalin, DA, Zelenkov, LE, Yu. Schmidt, E, Trofimov, BA & Vasilyev, AV 2022, 'Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species', European Journal of Organic Chemistry, vol. 2022, no. 30, e202200468. https://doi.org/10.1002/ejoc.202200468

APA

Borisova, M. A., Ryabukhin, D. S., Yu. Ivanov, A., Boyarskaya, I. A., Shabalin, D. A., Zelenkov, L. E., Yu. Schmidt, E., Trofimov, B. A., & Vasilyev, A. V. (2022). Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species. European Journal of Organic Chemistry, 2022(30), [e202200468]. https://doi.org/10.1002/ejoc.202200468

Vancouver

Borisova MA, Ryabukhin DS, Yu. Ivanov A, Boyarskaya IA, Shabalin DA, Zelenkov LE et al. Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species. European Journal of Organic Chemistry. 2022 Aug 12;2022(30). e202200468. https://doi.org/10.1002/ejoc.202200468

Author

Borisova, Marina A. ; Ryabukhin, Dmitry S. ; Yu. Ivanov, Alexander ; Boyarskaya, Irina A. ; Shabalin, Dmitrii A. ; Zelenkov, Lev E. ; Yu. Schmidt, Elena ; Trofimov, Boris A. ; Vasilyev, Aleksander V. / Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids : Experimental and Theoretical Study of Intermediate Cationic Species. In: European Journal of Organic Chemistry. 2022 ; Vol. 2022, No. 30.

BibTeX

@article{0fcfc810ca904e19824aa7b2b736892b,
title = "Transformations of 5-Hydroxy-1-pyrrolines in Strong Br{\o}nsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species",
abstract = "The reaction of 5-hydroxy-1-pyrrolines with arenes in TfOH at room temperature for 1 h afford 5-aryl-1-pyrrolines in 55–98 % yields. 5-Hydroxy-1-pyrrolines in TfOH or H2SO4 at room temperature for 0.5–1 h undergo dehydration with the formation of N-protonated forms of 3H-pyrroles, which were characterized by NMR. Upon hydrolysis, the N-protonated species give quantitatively the corresponding 3H-pyrroles. The intermediate cationic species derived from the protonation of 5-hydroxy-1-pyrrolines in Br{\o}nsted acids have been studied by means of NMR and DFT calculations. Plausible reaction mechanisms are discussed.",
keywords = "1-Pyrrolines, 3H-Pyrroles, Cations, Friedel-Crafts Reaction, Triflic acid",
author = "Borisova, {Marina A.} and Ryabukhin, {Dmitry S.} and {Yu. Ivanov}, Alexander and Boyarskaya, {Irina A.} and Shabalin, {Dmitrii A.} and Zelenkov, {Lev E.} and {Yu. Schmidt}, Elena and Trofimov, {Boris A.} and Vasilyev, {Aleksander V.}",
note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",
year = "2022",
month = aug,
day = "12",
doi = "10.1002/ejoc.202200468",
language = "English",
volume = "2022",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "30",

}

RIS

TY - JOUR

T1 - Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids

T2 - Experimental and Theoretical Study of Intermediate Cationic Species

AU - Borisova, Marina A.

AU - Ryabukhin, Dmitry S.

AU - Yu. Ivanov, Alexander

AU - Boyarskaya, Irina A.

AU - Shabalin, Dmitrii A.

AU - Zelenkov, Lev E.

AU - Yu. Schmidt, Elena

AU - Trofimov, Boris A.

AU - Vasilyev, Aleksander V.

N1 - Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/8/12

Y1 - 2022/8/12

N2 - The reaction of 5-hydroxy-1-pyrrolines with arenes in TfOH at room temperature for 1 h afford 5-aryl-1-pyrrolines in 55–98 % yields. 5-Hydroxy-1-pyrrolines in TfOH or H2SO4 at room temperature for 0.5–1 h undergo dehydration with the formation of N-protonated forms of 3H-pyrroles, which were characterized by NMR. Upon hydrolysis, the N-protonated species give quantitatively the corresponding 3H-pyrroles. The intermediate cationic species derived from the protonation of 5-hydroxy-1-pyrrolines in Brønsted acids have been studied by means of NMR and DFT calculations. Plausible reaction mechanisms are discussed.

AB - The reaction of 5-hydroxy-1-pyrrolines with arenes in TfOH at room temperature for 1 h afford 5-aryl-1-pyrrolines in 55–98 % yields. 5-Hydroxy-1-pyrrolines in TfOH or H2SO4 at room temperature for 0.5–1 h undergo dehydration with the formation of N-protonated forms of 3H-pyrroles, which were characterized by NMR. Upon hydrolysis, the N-protonated species give quantitatively the corresponding 3H-pyrroles. The intermediate cationic species derived from the protonation of 5-hydroxy-1-pyrrolines in Brønsted acids have been studied by means of NMR and DFT calculations. Plausible reaction mechanisms are discussed.

KW - 1-Pyrrolines

KW - 3H-Pyrroles

KW - Cations

KW - Friedel-Crafts Reaction

KW - Triflic acid

UR - http://www.scopus.com/inward/record.url?scp=85135873857&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/d046e988-a56c-3d16-9f28-ee5adce19f47/

U2 - 10.1002/ejoc.202200468

DO - 10.1002/ejoc.202200468

M3 - Article

AN - SCOPUS:85135873857

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 30

M1 - e202200468

ER -

ID: 99543607