Reactions of silver(I) acetate–iodine and thallium(I) acetate–iodine with substituted cyclopropanes

Abstract

Treatment of phenylcyclopropane with silver(I) acetate–iodine or thallium(I) acetate–iodine gives, as the major products, 1,3-disubstituted phenylpropanes resulting from cyclopropane ring opening, and in some cases, from solvolysis of intermediate iodo-acetates. Similar products are given with silver(I) trifluoroacetate–iodine but in this case aromatic iodination also occurs. Treatment of norcarane with the same reagents also results in ring opening, but here secondary products result from elimination and subsequent addition. Both substrates are less reactive than alkenes towards each reagent. Reaction mechanisms are discussed. The action of other reagent systems involving electrophilic iodine with phenylcyclopropane and norcarane is reported.