Reactivity of 2,6-diethyl-4,8-dimethyl-1,5-dioxo-s-hydrindacene towards radical, anionic and cationic germylation

The synthesis and diastereoisomeric resolution of 2,6-diethyl-4,8-dimethyl-1,5-dioxo-s-hydrindacene allowed the determination of the structure of the meso compound by X-ray diffractometry. The diastereoisomers were inactive towards radical germylation but reacted with acidic hydrogermanes or germylithium yielding α-germylated alcohols. By contrast, they were poorly reactive towards germylamines or SET reactions. This diketone acts as an efficient spin trap in radical hydrogermylation of alkenes.