Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/17940
Title: Photoinduced transformation of matrix-isolated methyl 2-pyrone-3-carboxylate into methyl 2-pyrone-5-carboxylate via intramolecular hydrogen shift in open-ring aldehyde–ketene
Authors: Reva, Igor 
Nowak, Maciej J. 
Lapinski, Leszek 
Fausto, Rui 
Issue Date: Feb-2008
Publisher: Elsevier
Serial title, monograph or event: Chemical Physics Letters
Volume: 452
Abstract: Photochemical transformations of methyl 2-pyrone-3-carboxylate (mp3c) were studied by matrix-isolation technique. The dominating primary photoreaction induced by UV (λ > 295 nm) light was α-bond cleavage leading to open-ring aldehyde–ketene. Another reaction characteristic of α-pyrones, isomerisation to the Dewar form, did not occur for mp3c. The ring-opening photoreaction was followed by intramolecular hydrogen shift and subsequent ring-closure reaction converting the aldehyde–ketene into methyl 2-pyrone-5-carboxylate (mp5c). Upon prolonged UV irradiation, mp3c completely transformed into mp5c and its Dewar isomer Dmp5c. Unequivocal identification of mp5c and Dmp5c photoproducts was enabled by exact knowledge of their experimental IR spectra, recorded in separate experiments.
URI: http://hdl.handle.net/10316/17940
DOI: 10.1016/j.cplett.2007.12.027
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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