Reactions of trialkylstannane anions R3Sn- with arylstannanes ArSnR'3.
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The reactions of trialkylstannane anions R<SUB>3</SUB>Sn<SUP>−</SUP> with arylstannanes ArSnR<SUB>3</SUB>′ have been investigated; trialkylstannane anions with arylstannanes at 50 °C gave substitution products ArSnR<SUB>3</SUB> in good yields. Most of these substitution products are diverted to reduction products ArH when <I>t</I>-butylamine for trapping free anionoids is present in the reaction mixture. These results are consistent with an initial tin–alkali metal exchange or an electron-transfer forming aryl anions and distannanes which subsequently react to the substitution products. Aryl radical intermediates by an electron-transfer process are also important in the reactions of trialkylstannane anions with electron-withdrawing groups-substituted arylstannanes, 1-naphthylstannanes, diphenylstannanes, and triphenylmethylstannane as good electron acceptor substrates.
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