Artículo
Structure and photochemical behaviour of 3-azido-acrylophenones: a matrix isolation infrared spectroscopy study
Fecha de publicación:
10/2011
Editorial:
Pergamon-Elsevier Science Ltd
Revista:
Tetrahedron
ISSN:
0040-4020
e-ISSN:
1464-5416
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
(Z)-3-Azido-3-methoxycarbonyl-2-chloro-acrylophenone (MACBP) has been synthesized, isolated in low temperature argon and xenon matrices and studied by FTIR spectroscopy, complemented by DFT(B3LYP)/6-311++G(d,p) calculations. The molecule was characterized both structurally and spectroscopically, and its photochemistry used to probe the mechanism of photo-induced conversion of 3-azido-acrylophenones into oxazoles. In situ UV irradiation (λ = 235 nm) of matrix-isolated MACBP yielded as primary photoproduct a 2H-azirine, which undergoes subsequent photoisomerization to methyl 4-chloro-5-phenyl-1,3-oxazole-2-carboxylate. In a competitive process, a ketenimine is also formed upon photolysis of MACBP. The reported results indicate that this ketenimine must be formed from the starting 3-azido-acrylophenone via a Curtius type concerted rearrangement.
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Articulos(CIDCA)
Articulos de CENTRO DE INV EN CRIOTECNOLOGIA DE ALIMENTOS (I)
Articulos de CENTRO DE INV EN CRIOTECNOLOGIA DE ALIMENTOS (I)
Citación
Lopes, Susy; Nunes, Cláudio M.; Gomez Zavaglia, Andrea; Pinho e Melo, Teresa M.V.D.; Fausto, Rui; Structure and photochemical behaviour of 3-azido-acrylophenones: a matrix isolation infrared spectroscopy study; Pergamon-Elsevier Science Ltd; Tetrahedron; 67; 40; 10-2011; 7794-7804
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