2H-Azirines from a concerted addition of alkylcarbenes to nitrile groups.
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.
Knoll
Wolfgang
W
Physical Organic and Structural Chemistry, Institute of Organic Chemistry, University of Vienna, Wahringer Strasse 38, A-1090 Vienna, Austria.
Mieusset
Jean-Luc
JL
Arion
Vladimir B
VB
Brecker
Lothar
L
Brinker
Udo H
UH
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
D000475:Alkenes; D001389:Azirines; D005650:Fumarates; C030011:carbene; C057444:fumaronitrile; D008697:Methane