2 H-Azirines from a Concerted Addition of Alkylcarbenes to Nitrile Groups†

…, JL Mieusset, VB Arion, L Brecker, UH Brinker

Index: Knoll, Wolfgang; Mieusset, Jean-Luc; Arion, Vladimir B.; Brecker, Lothar; Brinker, Udo H. Organic Letters, 2010 , vol. 12, # 10 p. 2366 - 2369

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Citation Number: 16

Abstract

Photolysis of aziadamantanes in the presence of fumaronitrile (FN) unexpectedly afforded conjugated 2 H-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 ...