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Fragmentation of Carbohydrate Anomeric Alkoxy Radicals: A New Synthesis of Chiral 1-Halo-1-iodo Compounds
51
Citations
26
References
2001
Year
Bioorganic ChemistryEngineeringOrganic ChemistryNew SynthesisChemistryHeterocycle ChemistryOrganometallic CatalysisBiochemistryChiral 1-Halo-1-iodoRadical (Chemistry)Asymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringHeterocyclicC1-c2 Radical FragmentationNatural SciencesCarbohydrate 1,2-HalohydrinsLess Carbon AtomHalogenation
One less carbon atom is found in 1-halo-1-iodo compounds obtained by C1-C2 radical fragmentation of carbohydrate 1,2-halohydrins. This fragmentation is achieved via the anomeric alkoxy radicals of the halohydrins, formed upon reaction with (diacetoxyiodo)benzene and iodine [Eq. (1); X=Cl, Br, I].
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