Benzyl cleavage in the oxidation of cycleanine by mercuric acetate

The dehydrogenation of cycleanine with mercuric acetate in 10% AcOH (at the boil) has been studied. It has been shown that it is accompanied by oxidative cleavage similar to benzyl cleavage under the action of electron impact. The main reaction product (without complexone) is the 8-(4-hydroxymethylphenoxy)-6,7-dimethoxy-2-methylisoquinolinium salt C₁₉H₂₀NO₄Cl·1.5H₂O, mp 196°C. The oxidation of cycleanine in the presence of ethylenediaminetetraacetic acid gave the mercuride C₁₉H₁₉NO₃I₂Hg·2H₂O, mp 240°C (water).