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Mechanistic Studies in the Attempted Synthesis of 5,5-Dimethyl-2-Isopropylidene-1,3-Cyclohexanedione

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In contrast to the corresponding cyclopentanedione derivative, 5,5-dimethyl-2-isopropyl-2-phenylsulfinyl-1,3-cyclohexanedione (3) does not undergo the expected cis-elimination of pherrylsulfenic acid on warming in CH2Cl2 to afford the title compound 1, but instead gives an equimolar mixture of 5,5-dimethyl-2-(1'-isopropyl-4',4'-dimethyl-2',6'-dioxocyclohexyl)-2-isopropyl-1,3-cyclohexanedione (9) and S-phenyl benzenethiosulfonate (10). These products result from dimerization of the 4,4-dimethyl-1-isopropyl-2,6-dioxocyclohexyl radical (7) and the phenylsulfinyl radical (8), respectively.

Affiliations: 1: Institut für Organische Chemie Universität, D-2000 Hamburg 13 Federal Republic of Germany


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