Iodine → HCID 13954642, compound

Participants

Reaction Steps

A stream of 3-5% ozone in oxygen was passed through a solution of (±)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptane from step (3) (1.20 g., 0.007 moles) in 35 ml. of methanol at -78° C. until the solution became light blue (ozone saturation). The excess ozone was removed by purging the cold reaction mixture with oxygen for 15 minutes. The cold reaction mixture was then poured into a stirred solution of 15 ml. of methanol, 4 ml. of glacial acetic acid, and 8 g. of sodium iodide and stirred for 30 minutes. Sodium thiosulfate solution (0.1N) was added to decompose the liberated iodine. Saturated NaHCO3 solution was then added until the mixture was slightly basic (pH 7.5). The aqueous mixture was extracted with ether, the extract washed with brine, and then dried over Na2SO4. Evaporation of the solvent afforded the product which was characterized by NMR. Yield: 1.12 g.

Provenance & Evidence