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

Yelizaveta Gorbunova; Dmitriy N. Zakusilo; Aleksander V. Vasilyev

doi:10.1016/j.tetlet.2019.02.047

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

Yelizaveta Gorbunova, Dmitriy N. Zakusilo, Aleksander V. Vasilyev

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

2 Scopus citations

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.

Original language	English
Article number	961-964
Journal	Tetrahedron Letters
Volume	60
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2019.02.047
State	Published - 4 Apr 2019

Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Electrophilic substitution
Indanones
Nitriles
Superacids

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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",

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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

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