Electrochemical Studies of Benzophenone and Fluorenone Imines, Amines and Diphenyldiazomethane.
AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH
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The redox behavior of several nitrogen containing derivatives of fluorenone and benzophenone has been studied. In this continuation of the study of possible precursors to carbene anoin radicals, diphenyldiazomethane Ph2CN2 has been studied in acetonitrile AN containing Me4NPF6 saturated as the supporting electrolyte. This was done to conform that the lifetime of the anoin radical Ph2CN2 is less than 1 ms in this electrolyte system. Parker and Bethell have recently reported that electroreduction of Ph2CN2 in AN-Me4NPF6 saturated at a hanging mercury drop electrode is electrochemically reversible at T 8 C and v 100 Vs. We have shown that their interpretation is in error, and that it is an artifact of unrecognized adsorption effects on the mercury electrode. The results reported here are consistent with previous findings using platinum as the cathode, i.e., the Ph2CN2 initially formed undergoes rapid loss of molecular nitrogen t to the 12 or 1 ms to yield the carbene anoin radical.
- Organic Chemistry
- Physical Chemistry