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Flow Photochemical Syntheses of trans -Cyclooctenes and trans -Cycloheptenes Driven by Metal Complexation.
Israel Journal of Chemistry 2020 March
trans -Cyclooctenes and trans -cycloheptenes have long been the subject of physical organic study, but the broader application had been limited by synthetic accessibility. This account describes the development of a general, flow photochemical method for the preparative synthesis of trans -cycloalkene derivatives. Here, photoisom erization takes place in a closed-loop flow reactor where the reaction mixture is continuously cycled through Ag(I) on silica gel. Selective complexation of the trans -isomer by Ag(I) during flow drives an otherwise unfavorable isomeric ratio toward the trans -isomer. Analogous photoreactions under batch-conditions are low yielding, and flow chemistry is necessary in order to obtain trans -cycloalkenes in preparatively useful yields. The applications of the method to bioorthogonal chemistry and stereospecific transannulation chemistry are described.
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