Ozonolysis of Enol Ethers. Part 10. Ozonization of Enol Ethers from 1,2‐ and 1,3‐Dicarbonyl Compounds: Direct Quantitative Synthesis of Phthalonic Acid Anhydride The results of ozonolyses of enol ethers from 1,2‐ and 1,3‐dicarbonyl compounds presented here strongly indicate that these reactions do not proceed via the established Criegee ozonolysis mechanism for nucleophilic CC bonds. The quantitative one‐step synthesis of phthalonic acid anhydride via ozonolysis of 2‐(methoxymethyliden)‐1 H ‐inden‐1,3(2 H )‐dione ( 28a ) is described. Furthermore, a revision of the theory of alkene ozonolysis in the presence of tetracyanoethylene (TCNE) is proposed on the basis of a single‐electron‐transfer (SET) chemistry.
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Schank et al. (2004) studied this question.
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