Electrochemical Functionalization of 1,3-Diisopropylbenzene

The anodic oxidation of 1,3‐diisopropylbenzene in methanol gave exclusively the desired dimethoxy‐functionalized product in excellent yield when potassium bromate was utilized as supporting electrolyte. Similar electrochemical conversions in other alcoholic solvents were not successful based on the...

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Veröffentlicht in:ChemSusChem 2010-07, Vol.3 (7), p.823-828
Hauptverfasser: Bohn, Martin A., Hilt, Gerhard, Bolze, Patrick, Gürtler, Christoph
Format: Artikel
Sprache:eng
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Zusammenfassung:The anodic oxidation of 1,3‐diisopropylbenzene in methanol gave exclusively the desired dimethoxy‐functionalized product in excellent yield when potassium bromate was utilized as supporting electrolyte. Similar electrochemical conversions in other alcoholic solvents were not successful based on the low conductivity of the mixture. The introduction of other alcohols could then be realized when the dimethoxy derivative was converted under SN1 conditions in alcohols used as solvent. Thereby, higher alcohols could be introduced in moderate yields and acceptable selectivities. Methanolics anodymous: The anodic oxidation of 1,3‐diisopropylbenzene in methanol leads to the bis‐methoxylated intermediate which can be converted under acidic conditions in appropriate alcohols into the corresponding bis‐alkoxylated products.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201000046