Electron transfer reactions of cyano substituted pyridines and quinolines with thermally generated diphenyl ketyl are reported. When E1/2(‐) for the heterocycle is less negative than ‐2V, electron transfer occurs from the ketyl to the heterocyclic base. In some cases the products obtained from the thermal reaction are the same as those obtained from the photochemical reaction with benzophenone and alcohols. In other cases different products are formed. Two bases, 2‐pyridinecarbonitrile and 2,4‐pyridinedicarbonitrile, undergo regiospecific reactions in which the course of the reaction is determined by the acidity of the medium. A mechanism in which the heterocyclic nitrogen is involved in the substitution process at the 2 position is proposed.

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