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Title

Photochemistry of α-diketones in carbohydrates: Anomalous norrish typea II photoelimination and norrish-yang photocyclization promoted by the internal carbonyl group

AuthorsÁlvarez-Dorta, Dimitri CSIC; León, Elisa I. CSIC ; Kennedy, Alan R.; Martín, Ángeles CSIC ORCID ; Pérez-Martín, Inés CSIC ORCID ; Riesco-Fagundo, Concepción CSIC; Suárez, Ernesto CSIC
KeywordsPhotochemistry
Radicals
Diketones
Carbohydrates
Cyclization
Issue Date24-Feb-2014
PublisherWiley-VCH
CitationChemistry - A European Journal 20(9): 2663-2671 (2014)
AbstractA series of four α‐diketones placed as 1α‐pyruvoyl tethers on D‐glucopyranose and D‐glucopyranosiduronic acid skeletons was prepared in order to determine the influence of captodative and stereoelectronic effects on the regioselectivity of the hydrogen atom transfer (HAT) in Norrish type II photochemical processes. We observed that the 1,5‐HAT regioselectivity can be switched between the two potentially abstractable syn‐1,3‐diaxial hydrogens at H6 and H8. Highly unusual photoproducts from Norrish type II photoelimination and Norrish–Yang photocyclization initiated by the excited internal carbonyl group were obtained, in some cases in excellent synthetic yield. The 1,5‐HAT transition state in the Norrish type II photoelimination was investigated by photochemical experiments in the crystalline state.
Publisher version (URL)https://doi.org/10.1002/chem.201303843
URIhttp://hdl.handle.net/10261/179894
DOI10.1002/chem.201303843
Identifiersdoi: 10.1002/chem.201303843
issn: 0947-6539
e-issn: 1521-3765
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