4-Pyridylnitrene and 2-pyrazinylcarbene

Wentrup, Curt, Reisinger, Ales and Kvaskoff, David (2013) 4-Pyridylnitrene and 2-pyrazinylcarbene. Beilstein Journal of Organic Chemistry, 9 754-760. doi:10.3762/bjoc.9.85

Author Wentrup, Curt
Reisinger, Ales
Kvaskoff, David
Title 4-Pyridylnitrene and 2-pyrazinylcarbene
Journal name Beilstein Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1860-5397
Publication date 2013-04-17
Year available 2013
Sub-type Article (original research)
DOI 10.3762/bjoc.9.85
Open Access Status DOI
Volume 9
Start page 754
End page 760
Total pages 7
Place of publication Frankfurt am Main, Germany
Publisher Beilstein - Institut zur Foerderung der Chemischen Wissenschaften
Language eng
Formatted abstract
Both flash vacuum thermolysis (FVT) and matrix photolysis generate 2-diazomethylpyrazine (22) from 1,2,3-triazolo[1,5- a]pyrazine (24). FVT of 4-azidopyridine (18) as well as of 24 or 2-(5-tetrazolyl)pyrazine (23) affords the products expected from the nitrene, i.e., 4,4’-azopyridine and 2- and 3-cyanopyrroles. Matrix photolyses of both 18 and 24 result in ring expansion of 4-pyridylnitrene/2-pyrazinylcarbene to 1,5-diazacyclohepta-1,2,4,6-tetraene (20). Further photolysis causes ring opening to the ketenimine 27.
Keyword Carbene-nitrene interconversion
Flash vacuum thermolysis
Matrix photochemistry
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
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