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

The Journal of Organic Chemistry
Martín J RiveiraMirta P Mischne

Abstract

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.

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