Nucleophilic Substitution in 1-Substituted 3-Iodobicyclopentanes. A New Synthetic Route to Functionalized Bicyclopentane Derivatives

Article abstract of DOI:10.1021/jo00049a030

Nucleophilic substitution of the iodine in 1-substituted 3-iodobicyclo<1.1.1>pentanes was investigated.The results of the reaction are strongly dependent on the nature of the nucleophile and the substituent.Whereas the trifluoromethyl derivative 2 is found to be inert in the reactions and gave substitution products only with organolithium reagents, the 1,3-diiodide 1 is much more reactive and affords normal substitution products with nitrogen bases and MeONa but gives <1.1.1>propellane with Grignard and organolithium reagents and with triaryl(allkyl)phosphines.Other synthesized 3-iodobicyclo<1.1.1>pentanes did not give substitution products.A general scheme for the transformations of 1 is also proposed.