OXYGEN-TRANSFER BY DISSOCIATIVE ELECTRON-TRANSFER - REACTION OF TETRANITROMETHANE WITH DIAZO-COMPOUNDS AND SULFIDES

In the absence of oxygen, diphenyldiazomethane is oxidized by tetranitromethane (TNM) to afford benzophenone and products derived from the diazoalkane radical cation, in yields strongly dependent on the reaction conditions. Sulfides were also found to undergo this oxygen transfer process with TNM. An initial dissociative electron transfer step is postulated to account for the observed results.