Nitration of Organolithiums and Grignards with Dinitrogen Tetroxide: Success at Melting Interfaces

摘要

Recently we reported that the sodium salts of 1,3,5,7- tetranitrocubane and 1,2,3,5,7-pentanitrocubance can be nitrated successfully with dinitrogen tetroxide in THF at low tempera- ture. These reactions apparently proceed by N_2O_4 oxidation of the anion to the radical and its combination with NO_2 (or N_2O_4). As far as we can find, these nitrations are the first successful examples of nitration of localized group IA orga- nometallics reported in the literature.