A Spectroscopic and Computational Study of a Photoinduced Cross-Dehydrogenative Coupling Reaction of a Stable Semiquinone Radical

Norrish-type-II reaction on a semiquinone radical: Stable semiquinone radicals serve as novel molecular platforms on which a Norrish-type-II photoreaction can be initiated. A detailed reaction scheme involving a 1,5-hydrogen transfer followed by a cyclization step that finally leads to a new CC bond formation could be verified. Transient absorption spectroscopy and DFT calculations trace convincingly the intermediates and transition states along the reaction path (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.