Photolysis of aryl azides generates nitrenes, and their subsequent rearrangement in the presence of water gives 3H-azepinones.
The reaction is performed in continuous flow in a photoreactor. Fine tuning of the reaction conditions allows minimization of secondary photochemical reactions. Professor Peter H. Seeberger and his co-workers explain this research result.
Seeberger Group | Max Planck Institute of Colloids and Interfaces, Potsdam, Germany
Peter H. Seeberger is Managing Director of the Max Planck Institute of Colloids and Interfaces in Potsdam, Germany and the Editor-in-Chief of the Beilstein Journal of Organic Chemistry. Alexander G. O’Brian, Farhan R. Bou-Hamdan and François Lévesque are Postdocs at the Max Planck Institute of Colloids and Interfaces.
The original research article is published in the Open Access Beilstein Journal of Organic Chemistry and is part of the Thematic Series Chemistry in flow systems II.
Bou-Hamdan, F. R.; Lévesque, F.; O’Brien, A. G.; Seeberger, P. H., Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones, Beilstein J. Org. Chem. 2011, 7, 1124–1129. doi:10.3762/bjoc.7.129
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