DIMETALLATION OF N-ETHYNYLPYRROLE AND SUBSEQUENT REGIOSPECIFIC DERIVATIZATION

The dilithium derivative N-lithioethynyl-2-lithiopyrrole generated fro m N-ethynylpyrrole or N-1,2-dichlorovinylpyrrole and two mol equivalen ts of n-butyllithium has been used for regiospecific substitution in t he 2-position by reaction with n-butyl iodide, N,N-dimethyl-formamide, sulfur, selenium and tellurium. The intermediate thiolates, selenolat es and tellurolates have been converted into bicyclic compounds by add ition of a mixture of t-butyl alcohol and hexamethylphosphoric triamid e.