Preparation of bicyclic 1,2,4-trioxanes from gamma,delta-unsaturated ketones.
Treatment of gamma,delta-unsaturated ketones with hydrogen peroxide and acid provides a rapid entry into the medicinally important 1,2,4-trioxane structure. Alkene substitution that stabilizes carbocationic intermediates proved to be important for the success of this transformation.
Ramirez
Armando P
AP
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Thomas
Andrew M
AM
Woerpel
K A
KA
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
C503429:1,2,4-trioxane; D000475:Alkenes; D006571:Heterocyclic Compounds; D007659:Ketones; D006861:Hydrogen Peroxide