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The Generation of Aryl Anions by Double Electron Transfer to Aryl Iodides from a Neutral Ground-State Organic Super-Electron Donor


  • We thank the EPRSC (S.Z.Z., D.W.T., F.S., and S.R.P.), the CVCP (Universities UK), and the University of Strathclyde (M.M.) for funding, the EPRSC National Mass Spectrometry Service Centre, Swansea for mass spectra, and Dr. K. Daasbjerg for helpful discussions.


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It takes two to cyclize: Aryl halides are reduced to aryl anions by double electron transfer from the neutral ground-state electron donor 1 (see scheme), as shown by the formation of a cyclic ketone (2). The reduced compound (3) is also formed. Calculations show that the loss of two electrons from 1 is both thermodynamically and kinetically viable and generates a more planar resonance-stabilized structure.