[3 + 2]-Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions.

ABSTRACT: 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.

SUBMITTER: Cludius-Brandt S 

PROVIDER: S-EPMC3778330 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature