Domino Self-Sensitized Photooxygenation of Conjugated Dienones for the Synthesis of 1,2,4-Trioxanes

The photochemical behavior of several dienones was studied under aerobic conditions. 2-Allylidene-1,3-cycloalkanediones prepared via Knoevenagel-type condensation between simple readily available 1,3-dicarbonyl substrates and α,β-unsaturated aldehydes afforded 1,2,4-trioxane derivatives upon UVA irr...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-03, Vol.84 (6), p.3671-3677
Main Authors: Riveira, Martín J, Martiren, Nadia L, Mischne, Mirta P
Format: Article
Language:English
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Summary:The photochemical behavior of several dienones was studied under aerobic conditions. 2-Allylidene-1,3-cycloalkanediones prepared via Knoevenagel-type condensation between simple readily available 1,3-dicarbonyl substrates and α,β-unsaturated aldehydes afforded 1,2,4-trioxane derivatives upon UVA irradiation in the presence of oxygen. This domino self-sensitized photooxygenation cascade of conjugated carbonyl systems proceeds stereoselectively and involves the formation of two new oxa-cycles, three new bonds (two C–O), and three stereocenters.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03279