Photorearrangement in a Semiquinone to Yield an Unusual 1,3-Carbon/Carbon Interaction and Spin Delocalization

@inproceedings{Kim1999PhotorearrangementIA,
  title={Photorearrangement in a Semiquinone to Yield an Unusual 1,3-Carbon/Carbon Interaction and Spin Delocalization},
  author={Yong Seol Kim and Cheryl D. Stevenson},
  year={1999}
}
Solutions of 1,4-bis(dihydroquininyl)-anthraquinone {(DHQ)2AQN} in either hexamethylphosphoramide (HMPA) or liquid ammonia undergo a photoinduced electron transfer from the solvent to the (DHQ)2AQN. The resulting anion radical {(DHQ)2AQN•-} yields coupling to the six (3 sets of 2 equivalent) protons on the anthraquinone moiety upon EPR analysis. The same anion radical can be generated via alkali metal reduction in tetrahydrofuran. Further exposure of the HMPA solution to visible light causes… CONTINUE READING