613672-24-5Relevant academic research and scientific papers
Cinnamonitrile as a precursor of a bi-centered electrophile in reactions with arenes in triflic acid
Gorbunova, Yelizaveta,Zakusilo, Dmitriy N.,Vasilyev, Aleksander V.
, p. 961 - 964 (2019)
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)CHCH2CN] 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.
