Sulfuric Acid → (1S,2R)-Indene oxide

Participants

Reaction Conditions

Reaction Steps

Into a 1000 ml four-neck flask, 259.5 g of an acetonitrile solution of 1,2-dibromoindan (corresponding to bromination of 0.559 mol of indene) was introduced. It was then heated to 40° C. To this solution, 86.57 g (0.839 mol) of 97% sulfuric acid was dropwise added at 40°-46° C. in a period of 1.5 hours. The resulting mixture was stirred at the same temperature for 5 hours. According to an HPLC analysis, about 15% of 1,2-dibromoindan was remaining in the mixture. To this mixture, 43.29 g of sulfuric acid was further added. The resulting mixture was stirred at 50°-60° C. for 1.5 hours. According to an HPLC analysis, 1,2-dibromoindan had almost disappeared yielding 11.0% of trans-amide derivative (III: R=CH3) and 25.3% of cis-oxazoline derivative (IV: R=CH3).

Provenance & Evidence