Application of electrogenerated triphenylmethyl anion as a base for alkylation of arylacetic esters and arylacetonitriles and isomerization of allylbenzenes was written by Suzuki, Shohei;Kato, Mitsuko;Nakajima, Shoichi. And the article was included in Canadian Journal of Chemistry in 1994.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:
Phenylacetic esters and phenylacetonitriles were alkylated with alkyl halides, at the position α to an ester or nitrile, either at room temperature (20°) or at -78°, by making use of electrogenerated triphenylmethyl anion (trityl anion). For example, regioselective alkylation of benzeneacetates gave α-alkylbenzeneacetates I (X = H, MeO; R1 = alkyl; R2 = Me, Et). Double-bond isomerization of allylbenzenes was also effectively accomplished using this electrogenerated base (EGB). In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).
2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts