Electrochemical oxidation of acylsilanes and their tosylhydrazones was written by Yoshida, Junichi;Itoh, Masanori;Matsunaga, Shinichiro;Isoe, Sachihiko. And the article was included in Journal of Organic Chemistry in 1992.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:
Oxidation potentials of acylsilanes were much less pos. than those of ketones and aldehydes. The effect of silicon is attributed to the rise of the HOMO level by the interaction between the C-Si σ orbital and the nonbonding p orbital of the carbonyl oxygen which in turn favors the electron transfer. Preparative electrochem. oxidation of acylsilanes proceeded smoothly, giving rise to facile cleavage of the C-Si bond and the introduction of nucleophiles such as alcs., water, and carbamates onto the carbonyl carbon. Electrochem. properties of tosylhydrazones of acylsilanes were also investigated. A decrease in oxidation potential of tosylhydrazones caused by silyl substitution was smaller than that for carbonyl compounds Preparative electrochem. oxidation of tosylhydrazones of acylsilanes gave the corresponding nitriles with consumption of a catalytic amount of electricity. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).
2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Recommanded Product: 2-Cyclohexylacetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts