Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 6, Pages 3671-3677Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03279
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Funding
- CONICET (PUE-2016)
- ANPCyT [PICT.2014-0408]
- Agencia Santafesina de Ciencia, Tecnica e Innovation (ASACTEI) [AC-2015-00005]
- Universidad Nacional de Rosario [BIO 426, BIO 514]
- CONICET
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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 alpha, beta-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.
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