dc.creator | Lopes, Susy | |
dc.creator | Nunes, Cláudio M. | |
dc.creator | Gomez Zavaglia, Andrea | |
dc.creator | Pinho e Melo, Teresa M.V.D. | |
dc.creator | Fausto, Rui | |
dc.date.accessioned | 2020-07-21T18:53:56Z | |
dc.date.accessioned | 2022-10-15T11:36:33Z | |
dc.date.available | 2020-07-21T18:53:56Z | |
dc.date.available | 2022-10-15T11:36:33Z | |
dc.date.created | 2020-07-21T18:53:56Z | |
dc.date.issued | 2011-10 | |
dc.identifier | 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 | |
dc.identifier | 0040-4020 | |
dc.identifier | http://hdl.handle.net/11336/109794 | |
dc.identifier | 1464-5416 | |
dc.identifier | CONICET Digital | |
dc.identifier | CONICET | |
dc.identifier.uri | https://repositorioslatinoamericanos.uchile.cl/handle/2250/4381563 | |
dc.description.abstract | (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. | |
dc.language | eng | |
dc.publisher | Pergamon-Elsevier Science Ltd | |
dc.relation | info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0040402011011483 | |
dc.relation | info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.tet.2011.07.084 | |
dc.rights | https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ | |
dc.rights | info:eu-repo/semantics/restrictedAccess | |
dc.subject | 3-Azido-acrylophenones | |
dc.subject | 2H-Azirines | |
dc.subject | Oxazoles | |
dc.subject | Ketenimines | |
dc.subject | Matrix isolation | |
dc.subject | IR spectroscopy | |
dc.subject | DFT(B3LYP)/6-311þþG(d,p) calculations | |
dc.subject | Conformational analysis | |
dc.subject | Photochemistry | |
dc.title | Structure and photochemical behaviour of 3-azido-acrylophenones: a matrix isolation infrared spectroscopy study | |
dc.type | info:eu-repo/semantics/article | |
dc.type | info:ar-repo/semantics/artículo | |
dc.type | info:eu-repo/semantics/publishedVersion | |