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The applicability of ketals was examined for masking the carbonyl group in N-tertiary 4-piperidones during the dehydrogenation using mercury-edta. Various 1,3-dioxolanes showed a different behaviour in dependence on the N-substituent. With simple aliphatic moieties mainly dehydrogenated but hydrolyzed products were received. These enaminones were also available from the dehydrogenations of the corresponding 4-piperidones. Similar applied to para-acyl-aromatic substituted derivatives but with less yields. Aromatic substituents bearing a neighbour group on ortho-position with participation gave rise to different oxidation products partially with preservation of the ketal structure

zeitschrift für naturforschung b

1,3-Dioxolane von N-substituierten 4-Piperidonen als Dehydrierungssubstrat / 1,3-Dioxolanes of N-Substituted 4-Piperidones as Substrates for Dehydrogenations