CH-acidity of substituted cycloalkanes

The value KD/KT of isotopic deutero- and tritium exchange reaction of hydrogen of phenylcycloalkanes with cyclohexylamine during catalysis by lithium cyclohexylamid and with dimethylsulfoxide during catalysis by KCH2SOCH3 and potassium tert.-butylate has been calculated, the kD/KT value decreases from 2.0-2.5 (for phenylcyclopentane and phenylcyclooctane) to 1.3-1.4 (for phenylcyclopropane). The conclusion is made that in the catalytic systems listed the stage of CH-acid ionization limits the rate of the reaction considered. Regularities of kD/kT values change in the reaction of phenylcycloalkane ionization are explained by the influence of structural rearrangement of hydrocarbon anionic fragments on the mechanism of the element action of proton transfer