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Abstract
Reactions between organogermyllithiums R 3GeLi and 3,5-di-t-butylorthoquinone mainly give digermanes but also O-germylcatechol and germadioxolanes. It appears that these reactions start after an initial single electron transfer (SET) which is supported by an ESR study of the reaction. ESR analysis shows the transient formation of an O-semiquinonic species and also germanium centered radicals R 3Ge · (stable at 20°C for R = Mes). The digermane formation can occur through germanium centered radicals duplication. But it appears that other by-reactions lead also to digermane as O-germylcatechol lithiogermolysis and unexpected successive SET reactions. All these reactions which work to form digermanes are highly dependent on the nature of the R group linked to germanium and specially on their steric hindrance.
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