Organic Electrode Reactions - Fundamentals and Applications of Organic Electrochemistry - page 130

There are two main methods for the generation
of EGBs, as shown in Eq. 5.6 . One method is
cathodic reduction of compounds with an
unsaturated moiety in aprotic solvents
containing quaternary ammonium salt as a
supporting electrolyte to generate the radical
anions or dianions, and the other one is
cathodic reductive deprotonation of active
hydrogen compounds to generate the
corresponding anions.
(5.6)
Cathodic reductive deprotonation of
2-pyrrolidone, a hindered phenol like
2,6- t -butyl-4-methylphenol, and
triphenylmethane generates the corresponding
anions. Since EGBs have quaternary
ammoniumcations (Q + ), the anions formed by
the treatment with EGB have high reactivity
( Figure 5.7 ) and hence this methodology is
highly useful for organic synthesis.