Transformations of 5‐Hydroxy‐1‐pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species
Marina A Borisova
1
,
Dmitry S Ryabukhin
1, 2
,
Alexander Yu Ivanov
3
,
Irina A Boyarskaya
4
,
Dmitrii A Shabalin
5
,
Lev E Zelenkov
6
,
Elena Yu Schmidt
5
,
Boris A. Trofimov
5
,
Publication type: Journal Article
Publication date: 2022-08-08
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
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 Brønsted acids have been studied by means of NMR and DFT calculations. Plausible reaction mechanisms are discussed.
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6
Total citations:
6
Citations from 2024:
3
(50%)
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Borisova M. A. 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. Vol. 2022. No. 30.
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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. Transformations of 5‐Hydroxy‐1‐pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species // European Journal of Organic Chemistry. 2022. Vol. 2022. No. 30.
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TY - JOUR
DO - 10.1002/ejoc.202200468
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202200468
TI - Transformations of 5‐Hydroxy‐1‐pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species
T2 - European Journal of Organic Chemistry
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
PY - 2022
DA - 2022/08/08
PB - Wiley
IS - 30
VL - 2022
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2022_Borisova,
author = {Marina A Borisova and Dmitry S Ryabukhin and Alexander Yu Ivanov and Irina A Boyarskaya and Dmitrii A Shabalin and Lev E Zelenkov and Elena Yu Schmidt and Boris A. Trofimov and Aleksander V Vasilyev},
title = {Transformations of 5‐Hydroxy‐1‐pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species},
journal = {European Journal of Organic Chemistry},
year = {2022},
volume = {2022},
publisher = {Wiley},
month = {aug},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202200468},
number = {30},
doi = {10.1002/ejoc.202200468}
}