Highly Efficient and Stereoselective Construction of 1-Iodo- or 1Phenylselenenyl-2-aryl-3-oxabicyclo[3.1.0]hexane from the Reaction of Arylmethylidenecyclopropylcarbinols with Iodine or Diphenyldiselenide

The reaction of arylmethylidenecyclopropylcarbinols 1 with iodine in the presence of potassium carbonate or diphenyldiselenide in the presence of sulfuryl chloride stereoselectively gives ring-closure product 1-iodo-2-aryl3-oxabicyclo[3.1.0]hexane or 1-phenylselenenyl-2-aryl-3oxabicyclo[3.1.0]hexane in good to high yields at room temperature. A plausible reaction mechanism has been proposed.