Source:http://linkedlifedata.com/resource/pubmed/id/21243679
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
4
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| pubmed:dateCreated |
2011-1-18
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| pubmed:abstractText |
Substituted 1-azidocyclopentenes and 1-azidocyclohexenes were photolyzed to generate 2,3-bridged 2H-azirines. In the case of bridgehead azirines with a six-membered carbocycle, detection by NMR spectroscopic analysis was possible, whereas even kinetically stabilized bridgehead azirines with a five-membered ring could not be characterized by low-temperature NMR spectroscopic analysis. Thus, a recent report on the latter heterocycles was corrected. Depending on the substitution pattern, irradiation of 1-azidocyclopentenes either led to products that can be explained on the basis of short-lived 2,3-bridged 2H-azirines, or gave secondary products generated from triplet nitrenes. The diverse photoreactivity of 2,3-bridged 2H-azirines was also studied by quantum chemical methods (DFT, CCSD(T), CASSCF(6,6)) with respect to the singlet and triplet energy surfaces. The ring-opening processes leading to the corresponding vinyl nitrenes were identified as key steps for the observed reactivity.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Jan
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| pubmed:issn |
1521-3765
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| pubmed:author | |
| pubmed:copyrightInfo |
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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| pubmed:issnType |
Electronic
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| pubmed:day |
24
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| pubmed:volume |
17
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
1128-36
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| pubmed:year |
2011
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| pubmed:articleTitle |
Highly strained 2,3-bridged 2H-azirines at the borderline of closed-shell molecules.
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| pubmed:affiliation |
Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany. klaus.banert@chemie.tu-chemnitz.de
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| pubmed:publicationType |
Journal Article
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