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

Article abstract of DOI:10.1016/S0040-4039(00)61221-2

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.