86260-83-5

Upstream product

• 88235-59-0 3-methyl-2-(1-naphthyl)-2H-azirine 
• 107-13-1 acrylonitrile 
• 832716-14-0 3-methyl-2-(4-nitro-1-naphthyl)-2H-azirine 
• 832716-12-8 3-methyl-2-(bromo-1-naphthyl)-2H-azirine 

Relevant academic research and scientific papers

Photochemistry of 2-(1-naphthyl)-2H-azirines in matrixes and in solutions: Wavelength-dependent C-C and C-N bond cleavage of the azirine ring

The photochemistry of 3-methyl-2-(1-naphthyl)-2H-azirine (1a) was investigated by the direct observation of reactive intermediates in matrixes at 10 K and by the characterization of reaction products in solutions. As already reported, the photolysis of the azirine 1a with the short-wavelength light (>300 nm) caused the C-C bond cleavage of the 2H-azirine ring to produce the nitrile ylide 2. However, the products derived from the C-N bond cleavage were exclusively obtained in the irradiation of 1a with the long-wavelength light (366 nm) both in matrixes and in solutions. When 1a was irradiated in the presence of O2 with the long-wavelength light, acetonitrile oxide (6) was produced through the capture of the biradical 4 generated by the C-N bond cleavage of 1a with O2. An introduction of a nitro group into the naphthyl ring of 1a resulted in an acceleration of the decomposition in the long-wavelength irradiation and an extension of the wavelength region where the products derived from the C-N bond cleavage were selectively obtained. On the basis of molecular orbital calculations with the INDO/S method, the reason for the wavelength-dependent selective C-C and C-N bond cleavage of the azirine ring of 1a is discussed.

Photochemical generation of acetonitrile oxide via the C-N bond cleavage of 3-methyl-2-(4-nitrophenyl)-2H-azirine

Acetonitrile oxide (2) is produced by the irradiation of the title azirine 1 in the presence of O2 in fluid solutions and in low-temperature matrices through the capture of the biradical 7 with O2, which is generated by the photochem

Control of C-C and C-N bond cleavage of 2H-azirine by means of the excitation wavelength: Studies in matrices and in solutions

The remarkable wavelengh-dependent photoreactions of 3-methyl-2-(1-naphthyl)-2H-azirine (1) were observed in matrices at 10 K and in solutions at room temperature. Irradiation of 1 with the long-wavelength light (366 nm) exclusively gave the products form