Details
| Original language | English |
|---|---|
| Pages (from-to) | 1745-1750 |
| Number of pages | 6 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 9 |
| Publication status | Published - 26 Aug 2013 |
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.
Keywords
- Azirines, Cycloaddition, Flow chemistry, Flow reactors, Inductive heating, Nitrile ylides, Photochemistry, Vinyl azides
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Beilstein Journal of Organic Chemistry, Vol. 9, 26.08.2013, p. 1745-1750.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - [3 + 2]-Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions
AU - Cludius-Brandt, Stephan
AU - Kupracz, Lukas
AU - Kirschning, Andreas
PY - 2013/8/26
Y1 - 2013/8/26
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.
AB - 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.
KW - Azirines
KW - Cycloaddition
KW - Flow chemistry
KW - Flow reactors
KW - Inductive heating
KW - Nitrile ylides
KW - Photochemistry
KW - Vinyl azides
UR - http://www.scopus.com/inward/record.url?scp=84885063356&partnerID=8YFLogxK
U2 - 10.3762/bjoc.9.201
DO - 10.3762/bjoc.9.201
M3 - Article
AN - SCOPUS:84885063356
VL - 9
SP - 1745
EP - 1750
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -