144443-32-3Relevant academic research and scientific papers
Synthesis of novel cage quaternary salts via nucleophilic substitution of 1,3-diiodobicyclo[1.1.1 ]pentane. Further evidence for a stable 3-iodo-1-bicyclo[1.1.1]pentyl cation
Adcock, James L.,Gakh, Andrei A.
, p. 4875 - 4878 (2007/10/02)
Nucleophilic substitution of 1,3-diiodobicyclo[1.1.1]pentane by tertiary amines and pyridines was investigated. The structure of cage quaternary salts obtained together with the observation of the competitive addition of pyridine in the reaction of [1.1.1]propellane with iodine indicate the existence of a relatively stable "hot intermediate" very close in its structure to a stabilized 3-iodo-1-bicyclo[1.1.1]pentyl cation.
Nucleophilic Substitution in 1-Substituted 3-Iodobicyclopentanes. A New Synthetic Route to Functionalized Bicyclopentane Derivatives
Adcock, James L.,Gakh, Andrei A.
, p. 6206 - 6210 (2007/10/02)
Nucleophilic substitution of the iodine in 1-substituted 3-iodobicyclopentanes 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 propellane with Grignard and organolithium reagents and with triaryl(allkyl)phosphines.Other synthesized 3-iodobicyclopentanes did not give substitution products.A general scheme for the transformations of 1 is also proposed.
