Hydrogen Peroxide → 1a,2a,3,6,6a,7a-Hexahydro-3,6-methanonaphtho[2,3-b]oxirene-2,7-dione

Participants

Reaction Conditions

Reaction Steps

A solution of tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione (14) (26.13 g, 150 mmol) in acetone (100 ml) was cooled to 0° C. on an ice-bath. To the solution was added saturated aqueous NaHCO3 (33 ml). To the mixture was added dropwise 34.5% aqueous hydrogen peroxide (142 ml) while keeping at 0° C. After the addition, the reaction mixture was stirred at 0° C. for 1 hr and then water (100 ml) was added. From the mixture solution, the product was extracted with diethyl ether (total 700 ml). The extract was washed with saturated aqueous NaCl and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to afford as the residue 4,5-epoxy-tricyclo[6.2.1.02,7]undec-9-ene-3,6-dione (15) (28.06 g, 148 mmol, 98.35% yield) in light ID yellowish white crystals.

Provenance & Evidence