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Mechanistic studies in the attempted synthesis of 5,5-dimethyl-2-isopropylidene-1,3-cyclohexanedione

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Abstract

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 phenylsulfenic 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-dioxocyclohexylradical (7) andthephenylsulfinyl radical (8), respectively.

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Authors and Affiliations

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

    C. P. Klaus & P. Margaretha

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  1. C. P. Klaus
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  2. P. Margaretha
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Diploma Thesis, University of Hamburg, 1990.

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Klaus, C.P., Margaretha, P. Mechanistic studies in the attempted synthesis of 5,5-dimethyl-2-isopropylidene-1,3-cyclohexanedione. Res Chem Intermed 16, 179–187 (1991). https://doi.org/10.1163/156856791X00246

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  • DOI: https://doi.org/10.1163/156856791X00246

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