M. Schmittel et A. Langels, ENOL RADICAL CATIONS IN SOLUTION - PART 12 - SYNTHESIS AND ELECTROCHEMICAL INVESTIGATIONS OF A STABLE ENOL LINKED TO A FERROCENE REDOX CENTER, Perkin transactions. 2, (3), 1998, pp. 565-571
The synthesis of the first stable enol linked to a ferrocene redox cen
tre is reported. After one-electron oxidation of this compound we rece
ive a persistent radical cation that can be activated by a second one-
electron oxidation step. The resulting enol dication undergoes rapid d
eprotonation to a diradical cation which finally furnishes two benzofu
rans as products. The mechanism of this reaction and the role of the f
errocene as a redox relay is discussed.