フェナントレンモノスルホン酸の転位

概要

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In connection with our earlier work on the substitution of phenanthrene, the rearrangement of phenanthrenemonosulfonic acids was investigated.<BR>Upon treatment of potassium 9-phenanthrenesulfonate with 77% sulfuric acid at 152°C for 5 hrs, a mixture of the 2-and 3-isomers containing a small amount of polysufonates and phenanthrene was obtained. The sulfonation product of phenanthrene containing the 1-sulfonate as obtained with the aid of a SO<SUB>3</SUB>-dioxane complex also gave a similar mixture by the same treatment. This indicates that rearrangement also takes place in the 1-sulfonate.<BR>The products were analyzed by thin layer chromatography on silica gel, developed by a chloroform-carbon tetrachloride mixture, after converting the sulfonic acids into hydroxy azo compounds through the corresponding phenanthrols. The 2-, 3-, and 9-sulfonates were alkali-fused into the corresponding phenanthrols. By coupling with benzenediazonium chloride, they gave the 1-, 4-, and 10-azo compounds. 1- Phenanthrol, however, afforded a mixture of two or three azo compounds.
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