Nucleophilic attack of acetylide anions at the two carbonyl moieties of para-quinones readily affords the corresponding diols. Subsequent reduction with stannous chloride affords a number of useful compounds, including 1, 4-bis [(trimethylsilyl) ethynyl] benzene, 1, 4-bis [(trimethylsilyl) ethynyl] naphthalene and 9, 10-bis [(trimethylsilyl) ethynyl] anthracene. Sequential attack by different acetylide anions followed by reduction provides a useful ...
