Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles was written by DiBiase, Stephen A.;Wolak, Raymond P. Jr.;Dishong, Dennis M.;Gokel, George W.. And the article was included in Journal of Organic Chemistry in 1980.Electric Literature of C8H13N This article mentions the following:
The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions An alternative hydrolysis method which involves KOCMe3 mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented. The isolated yields range from 21-93% and are highest for long-chain aliphatic nitriles such as cyanohexadecane. Other compounds that underwent oxidative hydrolysis were PhCH2CN, cyclohexaneacetonitrile, and cyclododecanecarbonitrile. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Electric Literature of C8H13N).
2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Electric Literature of C8H13N
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts