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dc.contributor.author
Lopes, Susy  
dc.contributor.author
Nunes, Cláudio M.  
dc.contributor.author
Gomez Zavaglia, Andrea  
dc.contributor.author
Pinho e Melo, Teresa M.V.D.  
dc.contributor.author
Fausto, Rui  
dc.date.available
2020-07-21T18:53:56Z  
dc.date.issued
2011-10  
dc.identifier.citation
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.issn
0040-4020  
dc.identifier.uri
http://hdl.handle.net/11336/109794  
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.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Pergamon-Elsevier Science Ltd  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
3-Azido-acrylophenones  
dc.subject
2H-Azirines  
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Oxazoles  
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Ketenimines  
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Matrix isolation  
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IR spectroscopy  
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DFT(B3LYP)/6-311þþG(d,p) calculations  
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Conformational analysis  
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Photochemistry  
dc.subject.classification
Otras Ingenierías y Tecnologías  
dc.subject.classification
Otras Ingenierías y Tecnologías  
dc.subject.classification
INGENIERÍAS Y TECNOLOGÍAS  
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  
dc.date.updated
2020-06-23T13:25:17Z  
dc.identifier.eissn
1464-5416  
dc.journal.volume
67  
dc.journal.number
40  
dc.journal.pagination
7794-7804  
dc.journal.pais
Estados Unidos  
dc.description.fil
Fil: Lopes, Susy. Universidad de Coimbra; Portugal  
dc.description.fil
Fil: Nunes, Cláudio M.. Universidad de Coimbra; Portugal  
dc.description.fil
Fil: Gomez Zavaglia, Andrea. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina  
dc.description.fil
Fil: Pinho e Melo, Teresa M.V.D.. Universidad de Coimbra; Portugal  
dc.description.fil
Fil: Fausto, Rui. Universidad de Coimbra; Portugal  
dc.journal.title
Tetrahedron  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0040402011011483  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.tet.2011.07.084