Oxidation of disubstituted 1-methylenedihydroisoquinoline enamides with lead tetraacetate results in a novel N→C oxidative rearrangement whereby esters of disubstituted 1-hydroxymethyl-3,4-dihydroisoquinoline are formed. An X-ray crystallographic structural determination for 6,7-dimethoxy1-[1-(p-methoxybenzoyloxy)-1 -methylethyl]-3,4-dihydroisoquinoline 4 is described.
G. R. Lenz, R. A. Lessor, P. W. Rafalko and Z. Kosarych, J. Chem. Soc., Perkin Trans. 1, 1993, 745 DOI: 10.1039/P19930000745
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