Propellane. Reaction of 1,4-Diiodobicyclohexane with tert-Butyllithium and with Potassium Atoms

Article abstract of DOI:10.1021/ja00349a048

The synthesis of 1,4-diiodobicyclo<2.1.1>hexane (5) is described.The reaction of 5 with tert-butyllithium in hexane gave the same type of products as previously observed in the reaction of 1,4-diiodonorbornane (2) with tert-butyllithium.Evidence has been presented indicating the latter reaction to proceed via <2.2.1>propellane as an intermediate, and it appears likely that the <2.1.1>propellane was involved in the former reaction.The reaction of 5 with potassium atoms in the gas phase led to the formation of an unstable compound which has been isolated in a nitrogen matrix and tentatively identified as the <2.1.1>propellane on the basis of its infrared spectrum.