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A Radical Alternative to the Anionic Oxy-Cope Rearrangement
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2002
Year
EngineeringSigmatropic RearrangementNatural SciencesRadical (Chemistry)Diversity-oriented SynthesisRadical AlternativeOrganic ChemistryRedox ChemistryStereoselective SynthesisChemistryAnionic Oxy-cope RearrangementHeterocycle ChemistryDeoxygenationBiomolecular Engineering
A radical alternative to the anionic oxy-Cope rearrangement is reported (e.g., see scheme; NIS = N-iodosuccinimide). In contrast to the sigmatropic rearrangement, this nonconcerted fragmentation–cyclization process is independent of the stereochemistry of the starting material.