Singlet Photoreactivity of 3-Methyl-2-phenyl-2H-azirine

Irradiation of 3-methyl-2-phenyl-2H-azirine (1) at 254 nm in argon matrices results in ylide 6. Similarly, laser flash photolysis (λ = 266 nm) of azirine 1 in acetonitrile yields ylide 6, which has a transient absorption with λmax at ~340 nm and a lifetime of 14 μs. Density functional theory calcula...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 70; no. 4; p. 413
Main Authors Weragoda, Geethika K., Das, Anushree, Sarkar, Sujan K., Sriyarathne, H. Dushanee M., Zhang, Xiaoming, Ault, Bruce S., Gudmundsdottir, Anna D.
Format Journal Article
LanguageEnglish
Published 2017
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Summary:Irradiation of 3-methyl-2-phenyl-2H-azirine (1) at 254 nm in argon matrices results in ylide 6. Similarly, laser flash photolysis (λ = 266 nm) of azirine 1 in acetonitrile yields ylide 6, which has a transient absorption with λmax at ~340 nm and a lifetime of 14 μs. Density functional theory calculations were preformed to support the characterisation of ylide 6 in solution and argon matrices. Irradiation of azirine 1 above 300 nm has previously been reported (J. Org. Chem. 2014, 79, 653) to yield triplet vinylnitrene in solution and ketenimine in cryogenic argon matrices. Thus, the photochemistry of azirine 1 is dependent on the irradiation wavelength.
ISSN:0004-9425
DOI:10.1071/CH16604