On the Catalytic Action of Japanese Acid Earth. XI. The Isomerisation of Aldehydes to Ketones and the Explanation of the Migration of the Radicals from the Standpoint of the Electronic Theory

Abstract

(1) All the phenomena hitherto ascribed to the characteristic catalytic action of Japanese acid earth can be explained by taking its strong electron-seeking property into consideration. Thus its ability to promote the hydrolysis of cane sugar or starch and the oxidation of pyrogallol and its property to give various oxidase-like colour reactions are all due to its selective adsorptive power for hydroxyl ion. The facts can similarly be explained that the dehydration or deamination of various organic compounds takes place through its catalytic action followed by the intramolecular rearrangement, as observed in the reaction of producing cyclopentane derivatives from cyclohexanol, cyclohexylamine or their methyl derivatives.The initial step of the formation of β,β′-dinaphthyl from naphthalene in the presence of the earth is the polarisation of the naphthalene molecule promoted by its electron-seeking property.(2) Several diarylacetaldehydes have been newly synthesised and found to rearrange themselves to give...