Reaction of thallium(I) acetate–iodine and silver(I) acetate–iodine with norborn-2-ene

Abstract

The reaction of norborn-2-ene with thallium(I) acetate–iodine in several solvents has been investigated, and the products have been compared with those arising from similar treatment of norbornene with silver(I) acetate–iodine. The product distribution in each case is indicative of an ionic pathway involving initial electrophilic addition of iodine followed largely by skeletal rearrangement characteristic of the bicyclo[2.2.1]heptyl system.