Oxidative Dearomatization: Synthesis of Functionalized Bicyclo[2.2.2]octenones, Sigmatropic Shift in Excited State, and Radical-Induced Cleavage of Cyclopropane Ring

Abstract

Synthesis of novel bicyclo[2.2.2]octenones endowed with a β,γ-enone system in which γ-carbon is substituted with an electron-withdrawing group from simple aromatics is described. Oxa-di-pi-methane reaction of bicyclo[2.2.2]octenones to functionalized bicyclo[3.3.0]octanes and their transformation to bicyclo[3.2.1]octane framework are also presented.

GRAPHICAL ABSTRACT

Keywords:

• Diels–Alder reaction
• oxa-di-pi-methane rearrangement
• pericyclic reaction
• photochemistry

ACKNOWLEDGMENTS

We thank D. Mhatre for crystal structure determination.

Notes

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