Alkylation of anionoid intermediates in the reaction of benzofuran with lithium in hexametapol

It is shown that the principal pathway in the reaction of benzofuran with a solution of lithium in hexametapol is opening of the furan ring of benzofuran to give a dilithium derivative. Mono- and dialkylation products are formed when the reaction mixture is treated with alkylating agents. It was established by the use of alkylating agents with different degrees of hardness that the oxygen atom is a softer polarizable center than the sp-hybridized carbanion center.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 22–23, January, 1978.