Abstract
Fission of dibenzo-p-dioxin (I) with metallic sodium in liquid ammonia afforded two kinds of phenolic substance, 2-hydroxyphenyl phenyl ether (II) and o-aminophenyl o-hydroxyphenyl ether (III). The same fission of 2, 7-dimethyldibenzo-p-dioxin (VI) also afforded two kinds of phenolic substance, 2-hydroxy-5-methylphenyl p-tolyl ether (VII) and 2-amino-4-methylphenyl 2-hydroxy-5-methylphenyl ether (X). Further reaction of (I) and (VI) with metallic sodium in liquid ammonia in the presence of potassium amide resulted in increased yield of (III) from (I) and that of (X) from (VI). This fact indicates that addition of potassium amide increased the yield of aminophenyl hydroxyphenyl ether. However, reaction of (I) with potassium amide alone failed to cause fission of (I) and (I) was recovered entirely.
Similar fission of 2, 7-dimethoxydibenzo-p-dioxin (XIV) afforded 2-hydroxy-5-methoxyphenyl p-methoxyphenyl ether (XV) and 2-hydroxy-4-methoxyphenyl m-methoxyphenyl ether (XVII), showing that there was no formation of an abnormal product.
