PERMANGANATE–PERIODATE OXIDATION: VI. THE OXIDATION OF VARIOUS ALIPHATIC COMPOUNDS

Abstract

A study was made of the reaction of the permanganate–periodate reagent with a wide variety of aliphatic alcohols, polyols, aldehydes, acids, oxy-acids, ketones, ethers, and esters. Saturated monols, ketones, and ethers, as well as acetic, pelargonic, pyruvic, lactic, and oxalic acids reacted only very slowly. Glycols, olefinic alcohols, and unsaturated acids were cleaved to give predictable end products. Activated alcohols and ethyl acetoacetate reacted at relatively high rates. Formic, glyoxylic, lactic, and malonic acids as well as 1,3-propanediol and 2,5-hexane dione reacted extensively and diethyl tartrate consumed as much oxidant as did tartaric acid. The oxidation of tetrahydrofurfuryl alcohol gave succinic acid instead of the expected tetrahydro-2-furoic acid. Saturated mono- and di-carboxylic acids, 3-hydroxy propionic acid, γ-valero lactone, and saturated esters were stable towards the reagent.