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Synlett 1990; 1990(6): 301-308
DOI: 10.1055/s-1990-34717
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Anodic Oxidation for the Syntheses of o- and p-Tropoquinone Mono- and Bisacetals

Akira Mori* , Hitoshi Takeshita
  • *Institute of Advanced Material Study, 86, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816, Japan
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Publication Date:
08 March 2002 (online)

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The preparation of o- and p-tropoquinone acetals by means of anodic oxidation is described, together with metal salt oxidations. The reactivities of acetals to Grignard reagents and photochemical and thermal reactions were investigated as well as the electrochemical reactions. Conformational changes of 4,4,5,5-tetramethoxy-2,6-cycloheptadien-1-ones and 6,6,7,7-tetramethoxy-2,4-cycloheptadien-1-one have been studied. 1. Introduction 2. Tropoquinone Acetals 2.1. Preparation 2.2. Mechanism of the Anodic Oxidation 3. Reactions of Tropoquinone Acetals 3.1. Alkylation 3.2. Thiele-Type Addition Reaction 3.3. Photochemistry 3.4. Thermal Cycloaddition Reaction 4. Properties of Tropoquinone Acetals 4.1. Cyclic Voltammetry 4.2. Conformational Changes of Bisacetals 5. Conclusion