Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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.
в: European Journal of Organic Chemistry, Том 2022, № 30, e202200468, 12.08.2022.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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