Cerium(IV)sulfate Oxidations of β-Aminoketones. Part V: Synthesis of Various Substituted 5-Oxo-2,6-methano-2-benzazocines

Article abstract of DOI:10.1002/ardp.19883211218

5-Oxo-2,6-methano-2-benzazocines are obtained by oxidation of various substituted methyl N-benzyl-4-oxo-3-piperidine carboxylates 1a, c-g with cerium(IV)sulfate.The corresponding diester 1h leads to a dehydrogenated methanobenzazocine 5h, additionally.By-products of nearly all oxidations are the corresponding 1,4,5,6-tetrahydro-3-(methoxycarbonyl)-pyridin-4-ones 3 and 1,4-dihydro-3-(methoxycarbonyl)pyridin-4-ones 4.