The Stability of Carboquone in Alcohols. I. Kinetics and Mechanisms of Degradation of 2,5-Bis (1-aziridinyl)-1,4-benzoquinone in Alcohols

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The kinetics and mechanisms of the degradation of 2,5-bis (1-aziridinyl)-1,4-benzoquinone (I) in alcohols were investigated and compared with those in aqueous solution obtained previously. The degradation of I in alcohols follows pseudo first-order kinetics as did that in aqueous solution. Degradation rates in a series of alcohols show a good correlation with Kosower's Z-values (empirical measures of solvent polarity). Degradation mechanisms of I in alcohols were investigated in methanol, where the degradation rate of I is relatively high, being suitable for detailed study. Five compounds were observed as degradation products of I in methanol, and the degradation process of I appeared to be rather complicated. However, the degradation behavior of I and some of these five degradation products in proton-rich methanol and methylate-rich methanol allowed us to deduce the chemical structures of all the degradation products : 5-(1-aziridinyl)-2-(2-methoxyethyl) amino-1,4-benzoquinone, 2,5-di (2-methoxyethyl) amino-1,4-benzoquinone, 5-(1-aziridinyl)-2-methoxy-1,4-benzoquinone, 2,5-dimethoxy-1,4-benzoquinone and 5-methoxy-2-(2-methoxyethyl) amino-1,4-benzoquinone. Their behavior also made it clear that I is degraded in methanol through a combination of two mechanisms : methanolysis of the aziridine ring, which is cleaved to a methoxyethylamino group, and substitution of the aziridine ring by a methoxy group. Therefore, the degradation mechanisms of I in methanol are concluded to be essentially the same as those in aqueous solution.
公益社団法人日本薬学会の論文
1985-07-25

The Stability of Carboquone in Alcohols. I. Kinetics and Mechanisms of Degradation of 2,5-Bis (1-aziridinyl)-1,4-benzoquinone in Alcohols

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