Anodic cyanation of tert-butylated anisoles: competitive aromatic additions and substitutions was written by Yoshida, Kunihisa;Takeda, Kazusada;Fueno, Takayuki. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1993.Computed Properties of C11H13N This article mentions the following:
The electrooxidation of several tert-butylated anisoles has been carried out in methanol containing sodium cyanide at a Pt anode in a divided cell. Two types of reactions occurred competitively, aromatic-ring addition and substitution. Increasing the level of tert-Bu substitution raises the relative extent of addition to the aromatic ring. The order of orientational preference for substitution of the aromatic hydrogen of alkylanisole cation radicals is explained in terms of the LUMO electron densities calculated for the cation radicals. The effect of structure on the oxidation potential of alkylanisoles has also been studied. Para substitution lowers the oxidation potential while ortho substitution raises the potential. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Computed Properties of C11H13N).
3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Computed Properties of C11H13N
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts