42758-54-3Relevant articles and documents
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
Inui, Hiroshi,Murata, Shigeru
, p. 2628 - 2636 (2005)
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.
para-Formylation of nitroarenes via vicarious nucleophilic substitution of hydrogen with tris(benzotriazol-1-yl)methane
Katritzky, Alan R.,Xie, Linghong
, p. 347 - 350 (2007/10/02)
Reaction of nitroarenes 1 with tris(benzotriazol-1-yl)methyl 2 anion afforded para-bis(benzotriazol-1-yl)methylated products 3 which, upon treatment with zinc bromide and hydrochloric acid, yielded the corresponding p-nitroarylaldehydes 4 in good yields.
