Leonard Spialter

Tetracyclohexylsilane: The resolution of an enigma

Abstract The conflicting experimental data and subsequent rationalizations in the literature on tetracyclohexylsilane are critically examined. It is established that the authentic compound, obtained by hydrogenation of tetraphenylsilane, can be synthesized by organolithium condensation, although a prior report mistakenly identified an impurity-caused product, tricyclohexyl(cyclohexyloxy)silane, as such. Studies on cyclohexyllithium and cyclopentylmethyllithium, as well as the synthesis of tricyclohexyl(cyclopentylmethyl)silane and its aromatic analog, demonstrate that the literature on the subject can be resolved without invoking isomerism due to rearrangement, restricted rotation, frozen conformation, or polymorphism.