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

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.