Addition 1,4 de divers organo- et organohalogeno-hydrogermanes sur la di-t-butyl-3,5 orthoquinone

Article abstract of DOI:10.1016/0022-328X(88)80524-2

The thermal 1,4-addition of triorganohydrogermanes R3GeH(R=Et, Ph) with 3,5-di-t-butylorthoquinone leads to their corresponding mono-O-germylated catechols in good yields.Similarly, the organohalohydrogermanes give the 2,2-di-organo- (or 2,2-organohalo)(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolanes after dehydrochlorination of transient mono-O-chlorogermylated catechols.Since these reactions are only slightly dependent on solvent and radical initiators, the mechanism probably involves monoelectronic transfer with the formation of a radical anion pair in the first step.The ESR measurements show the transient formation of a paramagnetico-semiquinonic species which supports the proposed mechanism.