Reactions of trialkyl(2-furyl)germanes with electrophilic reagents

Article abstract of DOI:10.1016/0022-328X(88)80334-6

The metallation (n-BuLi), alkylation (t-BuOH/H⁺), nitration (NO2⁺ BF4^-), bromination (NBS, dioxane dibromide (DDB)), acylation <(CF3CO)2O> and chlorination (chloramine T) reactions of (2-furyl)germanes were studied.Except for alkylation and bromination with DDB, the reactions involved electrophilic substitution of hydrogen atoms in position 5 or 3 of the furan ring.The alkylation reaction and bromination with DDB occur via ipso-substitution of the trialkylgermyl group.Dichlorocarbene generated by phase-transfer catalysis adds to the 2-germyl-substituted furan at the C₄=C₅ bond in the ring.Some of the above reactions were conducted with trimethyl(2-furyl)silane and 2-(t-butyl)furan, the silicon and carbon analogues of furylgermanes.The reactivities of the title compounds were compared.