Reactions of Trialkylstannane Anions R3Sn− with Arylstannanes ArSnR3′

Abstract

Abstract The reactions of trialkylstannane anions R3Sn− with arylstannanes ArSnR3′ have been investigated; trialkylstannane anions with arylstannanes at 50 °C gave substitution products ArSnR3 in good yields. Most of these substitution products are diverted to reduction products ArH when t-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.