Ring-Expansion Reactions of Epoxy Amides and Enamides: Functionalized Azetidines, Dihydrofurans, Diazocanes, or Dioxa-3-azabicyclonon-4-enes?
Suraj, K. C. Kumara Swamy
Abstract
Functionalized azetidines, 2,3-dihydrofurans, or the unorthodox dioxa-3-azabicyclonone-4-ene motifs are the products from transition metal-free reaction between N-oxiranylmethyl benzenesulfonamide and β-chloro-cinnamaldehyde, depending on whether one uses either NaI/K2CO3 or LiBr/K2CO3. These ring expansion reactions involve enamide (X-ray evidence) derived from N-oxiranylmethyl benzenesulfonamide and β-chloro-cinnamaldehyde as an intermediate. The N-oxiranylmethyl benzenesulfonamide itself upon heating gives readily separable and crystalline isomeric diazocanes that can be characterized by X-ray crystallography.
Topics & Concepts
ChemistryCinnamaldehydeRing (chemistry)EpoxyMedicinal chemistryPolymer chemistryStereochemistryOrganic chemistryCatalysisSynthesis and Catalytic ReactionsSynthesis of β-Lactam CompoundsAsymmetric Hydrogenation and Catalysis