NDLI: Highly Strained 2,3-Bridged 2H-Azirines at the Borderline of Closed-Shell $Molecules^{†}$

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Highly Strained 2,3-Bridged 2H-Azirines at the Borderline of Closed-Shell $Molecules^{†}$

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Schaarschmidt, Dieter Rüffer, Tobias Penk, Enrico Grimme, Stefan Banert, Klaus Saha, Biswajit Würthwein, Ernst-ulrich Lang, Heinrich Meier, Barbara
Description	Author Affiliation: Banert K ( Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany. klaus.banert@chemie.tu-chemnitz.de)
Abstract	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.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	4
Volume Number	17
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2011-01-24
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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