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Synthesis 1994; 1994(7): 675-677
DOI: 10.1055/s-1994-25542
short paper
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Synthesis of Δ2-1,3-Oxazolines and Δ2-1,3-Oxazines Using Potassium Fluoride on Alumina

Michael A. Mitchell* , Brian C. Benicewicz
  • *Polymers and Coatings Group, Los Alamos National Laboratory, Los Alamos, New Mexico 87545, USA
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Publication Date:
17 September 2002 (online)

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Potassium fluoride (40%) on alumina was used as a basic reagent for the ring closure of N-(β- or γ-haloalkyl)amides to give Δ2-1,3-oxazolines and Δ2-1,3-oxazines, respectively. Various 2-alkyl and 2-aryl derivatives were synthesized in moderate to high yield under relatively mild conditions (KF/Al2O3, solvent, room temperature). The procedure also facilitated simple workup and purification of the products. New compounds synthesized by this method are: 5-bromomethyl-2-phenyl-Δ2-1,3-oxazoline, 4,4-dimethyl-2-vinyl-Δ2-1,3-oxazoline, and 5-methylene-2-phenyl-Δ2-1,3-oxazine. The last compound represents the first authentic example of a 5-functionally substituted oxazine without substitution in the 4- or the 6- position.