2014
DOI: 10.1002/chem.201303843
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Photochemistry of α‐Diketones in Carbohydrates: Anomalous Norrish Type II Photoelimination and Norrish–Yang Photocyclization Promoted by the Internal Carbonyl Group

Abstract: A 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 photo… Show more

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Cited by 11 publications
(2 citation statements)
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“…The so obtained biradical 109.2 fragmentated, releasing Z photoenol 109.3 which upon heating underwent an intramolecular aldol reaction affording the final product 109.4. 342,343 This approach was a simple route to achieve the synthesis of densely functionalized cyclopentitols starting from pyranoses exhibiting a surprisingly diastereoselectivity.…”
Section: Biradicalsmentioning
confidence: 99%
“…The so obtained biradical 109.2 fragmentated, releasing Z photoenol 109.3 which upon heating underwent an intramolecular aldol reaction affording the final product 109.4. 342,343 This approach was a simple route to achieve the synthesis of densely functionalized cyclopentitols starting from pyranoses exhibiting a surprisingly diastereoselectivity.…”
Section: Biradicalsmentioning
confidence: 99%
“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] Azo dyes account for 60-70% of all dyes produced in the world, and the azo group usually undergoes reversible trans-cis photoisomerization which can also be exploited in the design of photo-switches, molecular motors, etc. [17][18][19][20][21] In contrast to azo-benzenes, heterocyclic azo compounds are less well investigated, although they have shown rich structural diversity, as well as chromophoric strength. The aromatic heterocyclic azo compounds having hydroxyl groups in ortho positions may give rise to two distinct isomers: azo and hydrazine form, which could coexist under certain experimental conditions.…”
Section: Introductionmentioning
confidence: 99%