74725-75-0Relevant academic research and scientific papers
Propellane. Reaction of 1,4-Diiodobicyclohexane with tert-Butyllithium and with Potassium Atoms
Wiberg, Kenneth B.,Walker, Frederick H.,Pratt, William E.,Michl, Josef
, p. 3638 - 3641 (2007/10/02)
The synthesis of 1,4-diiodobicyclohexane (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 propellane as an intermediate, and it appears likely that the 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 propellane on the basis of its infrared spectrum.
Reactions of Some Bicycloalkyl Iodides with Bromine
Wiberg, Kenneth B.,Pratt, William E.,Matturro, Michael G.
, p. 2720 - 2722 (2007/10/02)
The reactions of normally unreactive bicyclic iodides such as 1- and 7-iodonorbornane with bromine has been found to occur readily with the formation of the corresponding bromide.The reaction involves the formation of the complex RI*X2 as an intermediate and is accelerated by polar solvents.The reaction of 1-iodobicyclohexane with bromine led to rearranged products, showing that a cationic intermediate is involved.The data indicate that the IBr2- ion is one of the best of the known leaving groups for SN1 or SN2 reactions.The observation of a rapid reaction of the bridgehead bicyclooctyl iodides with bromine has led to a reexamination of the reaction of 1,4-diiodobicyclooctane with butyllithium.The previous report of the formation and trapping of the propellane in this reaction was found to be incorrect.
