Photochemical reactions of 1,2-diketones with silyl enol ethers

Title
Photochemical reactions of 1,2-diketones with silyl enol ethers
Author(s)
조대원박혜정[박혜정]윤웅찬[윤웅찬]김성홍[김성홍]손영구Patrick S. Mariano[Patrick S. Mariano]
Keywords
PHOTOINDUCED ELECTRON-TRANSFER; AROMATIC CARBONYL-COMPOUNDS; PET-OXIDATIVE CYCLIZATION; PHOTOADDITION REACTIONS; KETENE ACETALS; PHOTOCYCLIZATION REACTIONS; ALPHA-DIKETONES; REDUCTION; BENZIL; KETONES
Issue Date
201501
Publisher
SPRINGER
Citation
RESEARCH ON CHEMICAL INTERMEDIATES, v.41, no.1, pp.419 - 431
Abstract
Results arising from the current study demonstrate that UV irradiation-induced photoaddition reactions of the 1,2-diketones, acenaphthenequinone, 9,10-phenanthrenequinone, and benzil, with silyl enol ethers derived from propionaldehyde and isobutyraldehyde take place to form a variety of adducts. Product formation in these cases takes place mainly via two mechanistic pathways, one initiated by single electron transfer (SET) and the other by [2 + 2]-cycloaddition. In addition, observations show that the competition between these pathways depends on the nature of the substrates. An exploration of the photoreactions of acenaphthenequinone revealed that photoinduced SET is the predominant process occurring when the dimethyl-substituted silyl enol ether serves as a reactant, while cycloaddition and other excited state reactions become competitive with SET when the mono-methyl substituted silyl enol ether is used as a substrate. In the case of 9,10-phenanthrenequinone, photoreactions take place by [4 + 2]-cycloaddition routes regardless of the nature of the silyl enol ether employed. Finally, irradiation of benzil in the presence of both silyl enol ethers leads to exclusive or predominant formation of products arising by [2 + 2]-cycloaddition and photoinduced benzoyl radical forming alpha-cleavage.
URI
http://hdl.handle.net/YU.REPOSITORY/33683http://dx.doi.org/10.1007/s11164-013-1203-3
ISSN
0922-6168
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이과대학 > 화학생화학부 > Articles
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