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Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. / Gorbunova, Yelizaveta; Zakusilo, Dmitriy N.; Vasilyev, Aleksander V.

в: Tetrahedron Letters, Том 60, № 14, 961-964, 04.04.2019, стр. 961-964.

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

Harvard

Gorbunova, Y, Zakusilo, DN & Vasilyev, AV 2019, 'Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid', Tetrahedron Letters, Том. 60, № 14, 961-964, стр. 961-964. https://doi.org/10.1016/j.tetlet.2019.02.047

APA

Gorbunova, Y., Zakusilo, D. N., & Vasilyev, A. V. (2019). Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. Tetrahedron Letters, 60(14), 961-964. [961-964]. https://doi.org/10.1016/j.tetlet.2019.02.047

Vancouver

Gorbunova Y, Zakusilo DN, Vasilyev AV. Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. Tetrahedron Letters. 2019 Апр. 4;60(14):961-964. 961-964. https://doi.org/10.1016/j.tetlet.2019.02.047

Author

Gorbunova, Yelizaveta ; Zakusilo, Dmitriy N. ; Vasilyev, Aleksander V. / Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid. в: Tetrahedron Letters. 2019 ; Том 60, № 14. стр. 961-964.

BibTeX

@article{bf4d689bff92439f91d7f8472bd7d5aa,
title = "Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid",
abstract = " The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group. ",
keywords = "Electrophilic substitution, Indanones, Nitriles, Superacids, SUBSTITUTION, PHENOL, INVOLVEMENT, GATTERMANN, HOUBEN-HOESCH, KETONES, NITRILES, FESOTERODINE, BOND, TRIFLUOROMETHANESULFONIC ACID",
author = "Yelizaveta Gorbunova and Zakusilo, {Dmitriy N.} and Vasilyev, {Aleksander V.}",
year = "2019",
month = apr,
day = "4",
doi = "10.1016/j.tetlet.2019.02.047",
language = "English",
volume = "60",
pages = "961--964",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "14",

}

RIS

TY - JOUR

T1 - Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid

AU - Gorbunova, Yelizaveta

AU - Zakusilo, Dmitriy N.

AU - Vasilyev, Aleksander V.

PY - 2019/4/4

Y1 - 2019/4/4

N2 - The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

AB - The reaction of cinnamonitrile [PhCH = CHCN] with arenes in the superacid TfOH at room temperature for 1 h gave two types of compounds, 3-aryl-3-phenyl propionitriles [Ar(Ph)CHCH 2 CN] and/or 3-phenylindanones in 28–76% yield. The formation of these two reaction products depends on the nucleophilicity of the arene. In these reactions, carbocations generated upon the protonation of cinnamonitrile in TfOH behave as bi-centered electrophiles possessing reactive centers on the C3 carbon of the double bond and on the C1 carbon of the nitrile group.

KW - Electrophilic substitution

KW - Indanones

KW - Nitriles

KW - Superacids

KW - SUBSTITUTION

KW - PHENOL

KW - INVOLVEMENT

KW - GATTERMANN

KW - HOUBEN-HOESCH

KW - KETONES

KW - NITRILES

KW - FESOTERODINE

KW - BOND

KW - TRIFLUOROMETHANESULFONIC ACID

UR - http://www.scopus.com/inward/record.url?scp=85062271819&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2019.02.047

DO - 10.1016/j.tetlet.2019.02.047

M3 - Article

AN - SCOPUS:85062271819

VL - 60

SP - 961

EP - 964

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 14

M1 - 961-964

ER -

ID: 44001415