Reaction of Methylsulfinyl Carbanion with Substituted Phthalic Esters

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Abstract
The treatment of dimethyl 3-nitrophthalate (I) with a mixture of dimethyl sulfoxide and sodium methoxide, followed by the acidification of the resulting mixture with hydrochloric acid, gave azoxybenzene-2,2′,3,3′-tetracarboxylic acid (II) and 3-nitrophthalic acid (III). The similar treatment of dimethyl 4-nitrophthalate (IV) afforded 5-methoxy-2-nitroso-1,3-indanedione (V) and 4-methoxyphthalic acid (VI). The similar treatment of dimethyl 4-methoxyphthalate (XV) and dimethyl phthalate gave 2-chloro-2-methylthio-5-methoxy-1,3-indanedione (XVII) and 2-chloro-2-methylthio-1,3-indanedione (XIX) respectively. The general features of these reactions are described.

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