Helvetica Chimica Acta · 1954 · 19 citations · 4 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryStructure-activity RelationshipsSynthetic Medicinal ChemistryHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisOxidation ReactionsOxidation-reduction ReactionsSulfur ChemistryImine ReductionReduction Of Heterocycles
Abstract It is shown that LiAIH 4 reduces cyclic imides, namely 3,3‐disubstituted 2,5‐dioxo‐pyrrolidines and 2,6‐dioxo‐piperidines, primarily at the oxo‐group not adjacent to the two substituents. Hydroxylactames are formed as the first reduction products. Similarly, the same oxygen atom is replaced by sulfur by reaction with P 2 S 5 . This behaviour is ascribed to steric hindrance.
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