Article ID Journal Published Year Pages File Type
5218812 Tetrahedron 2012 8 Pages PDF
Abstract

Irradiation of alkyltropolone Diels-Alder adducts bearing β,γ-unsaturated ketone chromophores leads to fused polycyclic systems containing cyclopropane moieties in good yields. A detailed mechanistic study, which included the use of deuterium labeling in combination with HRMS and NMR experiments, revealed that the process is highly stereoselective, proceeds through the formation of allyl radical and ketene intermediates, and involves participation of the solvent.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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