Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones
Open Access
- 17 August 2011
- journal article
- research article
- Published by Beilstein Institut in Beilstein Journal of Organic Chemistry
- Vol. 7 (1) , 1124-1129
- https://doi.org/10.3762/bjoc.7.129
Abstract
Photolysis of aryl azides to give nitrenes, and their subsequent rearrangement in the presence of water to give 3H-azepinones, is performed in continuous flow in a photoreactor constructed of fluorinated ethylene polymer (FEP) tubing. Fine tuning of the reaction conditions using the flow reactor allowed minimization of secondary photochemical reactions.Keywords
This publication has 50 references indexed in Scilit:
- Enantiomerically Pure trans-β-Lactams from α-Amino Acids via Compact Fluorescent Light (CFL) Continuous-Flow PhotolysisJournal of the American Chemical Society, 2010
- Determination of Solvent‐Trapped Products Obtained by Photolysis of Aryl Azides in 2,2,2‐TrifluoroethanolChemistry – An Asian Journal, 2007
- New 1,3-dihydroazepin-2-one derivatives by [3,3]-sigmatropic rearrangement of suitably substituted 2-alkenylcyclopropyl isocyanatesCanadian Journal of Chemistry, 2004
- Photoisomerization of 3H -AzepinesJournal of Chemical Research, 1997
- The mechanism of photolysis of aromatic azidesRussian Chemical Reviews, 1992
- The photochemistry of phenyl azideRussian Chemical Reviews, 1992
- Photochemistry in industrial synthesisJournal of Photochemistry and Photobiology A: Chemistry, 1990
- Studies on diazepines. XXIX. Syntheses of 3H- and 5H-1,4-benzodiazepines from 3-azidoquinolines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Developments in Arylnitrene Chemistry: Syntheses and Mechanisms [New synthetic methods (31)]Angewandte Chemie International Edition in English, 1979
- Photoisomerization of 1-Aza-3,5,7-trimethylcyclohepta-4,6-dien-2-oneJournal of the American Chemical Society, 1964