Ag+-catalyzed oxidation of alkanal cyanohydrins by peroxydisulfate

TLDR: In this paper, the first stage of the reaction to 1-hydroxy-1-cyanoalkyl and 1-cyclohexyl radicals was shown to be competitive with the second stage.

Abstract: 1. Alkanal cyanohydrins (ACH) of general formula R(CH2)3CH(OH)CN are oxidized by the system S2O82−Ag+ to the acids R(CH2)3COOH and NCCHRCH2CH2COOH, indicating the competitive conversion of the ACH in the initial stage of the reaction to 1-hydroxy-1-cyanoalkyl and 1-cyanoalkoxyl radicals. 2. The oxidation of acetaldehyde cyanohydrin at 60° proceeds at approximately twice the rate of the oxidation of butanal, pentanal, isopentanal, and heptanal cyanohydrins, and approximately ten times as fast as that of tert-butanol.