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

Research output

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 languageEnglish
Article number961-964
JournalTetrahedron Letters
Volume60
Issue number14
DOIs
Publication statusPublished - 4 Apr 2019

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Carbon
Nitriles
Protonation
Reaction products
Temperature
cinnamonitrile
trifluoromethanesulfonic acid
propionitrile

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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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",
author = "Yelizaveta Gorbunova and Zakusilo, {Dmitriy N.} and Vasilyev, {Aleksander V.}",
year = "2019",
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language = "English",
volume = "60",
journal = "Tetrahedron Letters",
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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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U2 - 10.1016/j.tetlet.2019.02.047

DO - 10.1016/j.tetlet.2019.02.047

M3 - Article

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VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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M1 - 961-964

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