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 | |
| Publication status | Published - 4 Apr 2019 |
Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
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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.
In: Tetrahedron Letters, Vol. 60, No. 14, 961-964, 04.04.2019.Research output › › peer-review
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
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
VL - 60
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 14
M1 - 961-964
ER -