TY - JOUR A1 - Cludius-Brandt, Stephan A1 - Kupracz, Lukas A1 - Kirschning, Andreas T1 - [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 1745 EP - 1750 SN - 1860-5397 DO - 10.3762/bjoc.9.201 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.201 KW - azirines KW - cycloaddition KW - flow chemistry KW - flow reactors KW - inductive heating KW - nitrile ylides KW - photochemistry KW - vinyl azides N2 - The photodenitrogenation of vinyl azides to 2H-azirines by using a photoflow reactor is reported and compared with thermal formation of 2H-azirines. Photochemically, the ring of the 2H-azirines was opened to yield the nitrile ylides, which underwent a [3 + 2]-cycloaddition with 1,3-dipolarophiles. When diisopropyl azodicarboxylate serves as the dipolarophile, 1,3,4-triazoles become directly accessible starting from the corresponding vinyl azide. ER -