title: 2H-Azirines from a concerted addition of alkylcarbenes to nitrile groups.
abstract: Photolysis of aziadamantanes in the presence of fumaronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which a concerted pathway is postulated. The novel outcome of the reaction is favored by the prior formation of a carbene-alkene complex, a type of adduct that only recently has been described.
authors.affiliation: Physical Organic and Structural Chemistry, Institute of Organic Chemistry, University of Vienna, Wahringer Strasse 38, A-1090 Vienna, Austria.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Knoll
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Mieusset
authors.forename: Vladimir B
authors.initials: VB
authors.lastname: Arion
authors.forename: Lothar
authors.initials: L
authors.lastname: Brecker
authors.forename: Udo H
authors.initials: UH
authors.lastname: Brinker
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D005650:Fumarates / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010782:Photolysis; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001389:Azirines; D005650:Fumarates; C030011:carbene; C057444:fumaronitrile; D008697:Methane