4-Pyridylnitrene and 2-pyrazinylcarbene

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-cya...

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Autores principales: Wentrup, Curt, Reisinger, Ales, Kvaskoff, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678510/
https://www.ncbi.nlm.nih.gov/pubmed/23766787
http://dx.doi.org/10.3762/bjoc.9.85
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author Wentrup, Curt
Reisinger, Ales
Kvaskoff, David
author_facet Wentrup, Curt
Reisinger, Ales
Kvaskoff, David
author_sort Wentrup, Curt
collection PubMed
description 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.
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spelling pubmed-36785102013-06-13 4-Pyridylnitrene and 2-pyrazinylcarbene Wentrup, Curt Reisinger, Ales Kvaskoff, David Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-04-17 /pmc/articles/PMC3678510/ /pubmed/23766787 http://dx.doi.org/10.3762/bjoc.9.85 Text en Copyright © 2013, Wentrup et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Wentrup, Curt
Reisinger, Ales
Kvaskoff, David
4-Pyridylnitrene and 2-pyrazinylcarbene
title 4-Pyridylnitrene and 2-pyrazinylcarbene
title_full 4-Pyridylnitrene and 2-pyrazinylcarbene
title_fullStr 4-Pyridylnitrene and 2-pyrazinylcarbene
title_full_unstemmed 4-Pyridylnitrene and 2-pyrazinylcarbene
title_short 4-Pyridylnitrene and 2-pyrazinylcarbene
title_sort 4-pyridylnitrene and 2-pyrazinylcarbene
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678510/
https://www.ncbi.nlm.nih.gov/pubmed/23766787
http://dx.doi.org/10.3762/bjoc.9.85
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