Abstract

The reaction of benzopinacol with the non-ionic bases butyllithium and phosphazene P4 leads to the formation of the corresponding ketyl radical anions, which have been characterized by EPR/ENDOR spectroscopy. This conversion has a high efficiency. Such a reversed pinacol reaction can be used for a controlled release of ketyl radicals. Moreover, the nature of the base has a marked effect on the association of the ketyl radical anion and the counterions. This illustrates the importance of ion pairing for reductive coupling.

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