Abstract
Irradiation of 2-azidovinylbenzene (1) in a cryogenic argon matrix with a 254 nm bandpass filter results in 2-phenyl-2H-azirine (2) as the major product, some ketenimine 5, and a small amount of cis-1, whereas irradiation of vinyl azide 1 with light above 300 nm forms only azirine 2 and ketenimine 5. Prolonged irradiation of azirine 2 through a 254 nm bandpass filter produces ylide 3 selectively. Laser flash photolysis with excitation at 308 nm demonstrated that azirine 2 forms triplet vinylnitrene 4 (λ ∼ 440 nm), whereas vinyl azide 1 does not exhibit transient absorption on a nanosecond timescale. DFT calculations (B3LYP/6-31 + G(d)) were used to aid the characterization of the photoproducts and to support the proposed formation mechanisms.
Published Version
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