Tuning reactivity and chemoselectivity in electron transfer initiated cyclization reactions: Applications to carbon-carbon bond formation

JR Seiders, L Wang, PE Floreancig

Index: Seiders II, John R.; Wang, Lijun; Floreancig, Paul E. Journal of the American Chemical Society, 2003 , vol. 125, # 9 p. 2406 - 2407

Full Text: HTML

Citation Number: 50

Abstract

In this communication, we demonstrate that the scope of our electron transfer initiated cyclization reaction can be significantly broadened by exploiting the relationship between the oxidation potentials of homobenzylic ethers and the mesolytic benzylic carbon-carbon bond dissociation energies of their radical cations. By lowering the oxidation potential of the electrophore and the benzylic carbon-carbon bond dissociation energy, we can initiate ...