Standard

Zooming in on the hydrated imidazoline ring expansion : Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines. / Lavit, Kseniya; Reutskaya, Elena; Grintsevich, Sergey; Sapegin, Alexander; Krasavin, Mikhail.

в: Tetrahedron Letters, Том 61, № 42, 152423, 15.10.2020.

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

Harvard

Lavit, K, Reutskaya, E, Grintsevich, S, Sapegin, A & Krasavin, M 2020, 'Zooming in on the hydrated imidazoline ring expansion: Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines', Tetrahedron Letters, Том. 61, № 42, 152423. https://doi.org/10.1016/j.tetlet.2020.152423

APA

Lavit, K., Reutskaya, E., Grintsevich, S., Sapegin, A., & Krasavin, M. (2020). Zooming in on the hydrated imidazoline ring expansion: Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines. Tetrahedron Letters, 61(42), [152423]. https://doi.org/10.1016/j.tetlet.2020.152423

Vancouver

Lavit K, Reutskaya E, Grintsevich S, Sapegin A, Krasavin M. Zooming in on the hydrated imidazoline ring expansion: Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines. Tetrahedron Letters. 2020 Окт. 15;61(42). 152423. https://doi.org/10.1016/j.tetlet.2020.152423

Author

Lavit, Kseniya ; Reutskaya, Elena ; Grintsevich, Sergey ; Sapegin, Alexander ; Krasavin, Mikhail. / Zooming in on the hydrated imidazoline ring expansion : Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines. в: Tetrahedron Letters. 2020 ; Том 61, № 42.

BibTeX

@article{9773cd2a1e58433781726a8d2c4f8cb7,
title = "Zooming in on the hydrated imidazoline ring expansion: Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines",
abstract = "The influence of electronic factors on the rates of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines has been examined. Electron-withdrawing substituents on the aroyl group were found to weakly accelerate the reaction (in linear correlation with the Hammett σp constants). Much stronger influence came from the nitrogen-bound aromatic group which gave a strong linear correlation with the Hammett σp− constants. For electron-deficient heteroaromatics and nitroaromatics, the migration was nearly instantaneous in basic medium. These findings will significantly impact the planning of mechanistically related transformations of N-(2-aminoethyl) lactams through the hydrated imidazoline ring expansion (HIRE) process.",
keywords = "Addition-elimination, Base-promoted reaction, Hammett σ and σ constants, Hydrated imidazoline ring expansion, N → N′ acyl migration, Hammett σp and σp− constants, 1-ARYL-2-PHENYL-2-IMIDAZOLINES, HYDROLYSIS, Hammett sigma(p) and sigma(-)(p) constants, BASICITY-RATE, N -> N' acyl migration",
author = "Kseniya Lavit and Elena Reutskaya and Sergey Grintsevich and Alexander Sapegin and Mikhail Krasavin",
year = "2020",
month = oct,
day = "15",
doi = "10.1016/j.tetlet.2020.152423",
language = "English",
volume = "61",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "42",

}

RIS

TY - JOUR

T1 - Zooming in on the hydrated imidazoline ring expansion

T2 - Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines

AU - Lavit, Kseniya

AU - Reutskaya, Elena

AU - Grintsevich, Sergey

AU - Sapegin, Alexander

AU - Krasavin, Mikhail

PY - 2020/10/15

Y1 - 2020/10/15

N2 - The influence of electronic factors on the rates of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines has been examined. Electron-withdrawing substituents on the aroyl group were found to weakly accelerate the reaction (in linear correlation with the Hammett σp constants). Much stronger influence came from the nitrogen-bound aromatic group which gave a strong linear correlation with the Hammett σp− constants. For electron-deficient heteroaromatics and nitroaromatics, the migration was nearly instantaneous in basic medium. These findings will significantly impact the planning of mechanistically related transformations of N-(2-aminoethyl) lactams through the hydrated imidazoline ring expansion (HIRE) process.

AB - The influence of electronic factors on the rates of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines has been examined. Electron-withdrawing substituents on the aroyl group were found to weakly accelerate the reaction (in linear correlation with the Hammett σp constants). Much stronger influence came from the nitrogen-bound aromatic group which gave a strong linear correlation with the Hammett σp− constants. For electron-deficient heteroaromatics and nitroaromatics, the migration was nearly instantaneous in basic medium. These findings will significantly impact the planning of mechanistically related transformations of N-(2-aminoethyl) lactams through the hydrated imidazoline ring expansion (HIRE) process.

KW - Addition-elimination

KW - Base-promoted reaction

KW - Hammett σ and σ constants

KW - Hydrated imidazoline ring expansion

KW - N → N′ acyl migration

KW - Hammett σp and σp− constants

KW - 1-ARYL-2-PHENYL-2-IMIDAZOLINES

KW - HYDROLYSIS

KW - Hammett sigma(p) and sigma(-)(p) constants

KW - BASICITY-RATE

KW - N -> N' acyl migration

UR - http://www.scopus.com/inward/record.url?scp=85090592361&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/e74ab283-1730-3543-8f3d-8e4ed01128d6/

U2 - 10.1016/j.tetlet.2020.152423

DO - 10.1016/j.tetlet.2020.152423

M3 - Article

AN - SCOPUS:85090592361

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 42

M1 - 152423

ER -

ID: 62462942