Benzyl cleavage in the oxidation of cycleanine by mercuric acetate
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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).
KeywordsAlkaloid Oxidative Cleavage Activity Grade Mercury Compound Main Reaction Product
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- 1.J. Szmuszkovic, Advances in Organic Chemistry,4, 1 (1963).Google Scholar
- 2.L. Fieser and M. Fieser, Reagents for Organic Synthesis, Wiley, New York, Vol. 3, (1972), p. 194.Google Scholar
- 3.S. M. Kupchan, Recent Advances in the Chemistry of Tumor Inhibitors of Plant Origin. International Symposium on Natural Products. “Phytochemistry of the Balkan Flora,” Varna, October 14–18, 1971, Bulgaria, Plenary Lecture.Google Scholar
- 5.O. P. Belichenko and O. N. Tolkachev, Khim. Prir. Soedin., 125 (1976).Google Scholar
- 6.O. P. Belichenko, O. N. Tolkachev, and D. A. Fesenko, Khim. Prir. Soedin., 662 (1977).Google Scholar