NMR Study on the Electrochemically Generated Triphenylmethyl Anion
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Abstract
The <sup>13</sup>C and <sup>1</sup>H NMR spectra of the triphenylmethyl anion, which had been generated by an electrochemical reduction of triphenylmethane in dimethylformamide at −40 °C, were successfully obtained. An anion having a tetrabutylammonium counter cation had <sup>13</sup>C chemical shifts similar to those for an anion with a lithium counter cation. An examination of the <sup>1</sup>H NMR spectra revealed that the reaction is a one-electron reaction. Experiments conducted under temperature control showed that the anion is fairly stable below −20 °C. Decomposition of the anion above −20 °C was suggested to be hydrogen abstraction from the <i>β</i>-position of a tetrabutylammonium cation by a triphenylmethyl anion (Hofmann decomposition of the ammonium cation).
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 68(3), 759-763, 1995-03-15
The Chemical Society of Japan