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

被引：10

作者：

Weragoda, Geethika K. ^{[1
]}

Das, Anushree ^{[1
]}

Sarkar, Sujan K. ^{[1
]}

Sriyarathne, H. Dushanee M. ^{[1
]}

Zhang, Xiaoming ^{[1
]}

Ault, Bruce S. ^{[1
]}

Gudmundsdottir, Anna D. ^{[1
]}

机构：

[1] Univ Cincinnati, Dept Chem, POB 210172, Cincinnati, OH 45221 USA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2017年 / 70卷 / 04期

基金：

美国国家科学基金会;

关键词：

N BOND-CLEAVAGE; NITRILE YLIDES; TRIPLET VINYLNITRENE; PHOTOCHEMISTRY; 2H-AZIRINES; PHOTOLYSIS; ENERGIES; MATRICES;

D O I：

10.1071/CH16604

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Irradiation of 3-methyl-2-phenyl-2H-azirine (1) at 254nm in argon matrices results in ylide 6. Similarly, laser flash photolysis (lambda=266nm) of azirine 1 in acetonitrile yields ylide 6, which has a transient absorption with lambda(max) at similar to 340nm and a lifetime of 14 mu s. Density functional theory calculations were preformed to support the characterisation of ylide 6 in solution and argon matrices. Irradiation of azirine 1 above 300nm 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.

引用

页码：413 / 420

页数：8

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