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...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.85 |
| _version_ | 1818413967855321088 |
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| author | Curt Wentrup Ales Reisinger David Kvaskoff |
| author_facet | Curt Wentrup Ales Reisinger David Kvaskoff |
| author_sort | Curt Wentrup |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-14T11:11:37Z |
| format | Article |
| id | doaj.art-58e6675ee8cf4c15b0b5b4472d94c638 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T11:11:37Z |
| publishDate | 2013-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-58e6675ee8cf4c15b0b5b4472d94c6382022-12-21T23:04:14ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-04-019175476010.3762/bjoc.9.851860-5397-9-854-Pyridylnitrene and 2-pyrazinylcarbeneCurt Wentrup0Ales Reisinger1David Kvaskoff2School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, AustraliaSchool of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, AustraliaSchool of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, AustraliaBoth 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.https://doi.org/10.3762/bjoc.9.85carbene–nitrene interconversiondiazepinesflash vacuum thermolysismatrix photochemistrynitrile ylidesreactive intermediates |
| spellingShingle | Curt Wentrup Ales Reisinger David Kvaskoff 4-Pyridylnitrene and 2-pyrazinylcarbene Beilstein Journal of Organic Chemistry carbene–nitrene interconversion diazepines flash vacuum thermolysis matrix photochemistry nitrile ylides reactive intermediates |
| 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 | carbene–nitrene interconversion diazepines flash vacuum thermolysis matrix photochemistry nitrile ylides reactive intermediates |
| url | https://doi.org/10.3762/bjoc.9.85 |
| work_keys_str_mv | AT curtwentrup 4pyridylnitreneand2pyrazinylcarbene AT alesreisinger 4pyridylnitreneand2pyrazinylcarbene AT davidkvaskoff 4pyridylnitreneand2pyrazinylcarbene |