In 1897 it ivas observed (1) that potassium iodide (in hot alcohol or acetone) converts ethyl p-bromobenzenesulfonate to ethyl iodide. Many years later, methyl and ethyl iodides (2, 3) and ethyl a-iodopropionate (4) were prepared in good yield by the action of the same reagent (in boiling water or alcohol) on the corresponding p-toluenesulfonates. The method was next applied (5) to the preparation of diisopropylidene-6-iododesoxygalactose from the 6-tosyl derivative, with the improvement of using Finkelstein's reagent (6), namely, sodium iodide dissolved in acetone. Further research has, however, been mainly confined to study of the behavior of tosyl esters of sugar derivatives (7) towards the reagent and it has been found that a primary tosyloxy group is much more reactive than a secondary in such aldo-sugar derivatives as methyl 2,3,4,6tetratosyl-iS-D-glucoside.The reaction is usually found to proceed as an alkyl-oxygen fission (8) in accordance with the equation: ! SUMMARYThe reaction of certain esters of p-toluenesulfonic acid with sodium iodide dissolved in acetone has been studied. Their reactivities are found to be in the same relative order as those of the corresponding organic chlorides towards the same reagent.The tosyl esters of isopropyl alcohol and thymol have been obtained in crystalline condition. The less reactive esters studied may be prepared in good yield in the presence of pyridine at room temperature.Pittsburgh 13, Pa.

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In connection with certain studies on sulfonic esters of sugar derivatives, a sample of diethyl tetra-O-p-tolylsulfonylmucate (p-tolylsulfonyl = "tosyl"; Ts) was desired. Its preparation, by reaction of diethyl mucate (galactarate) with p-toluenesulfonyl chloride in pyridine, was expected to be a simple procedure. However, under all conditions tried, we were unable to isolate any of the compound.6Pittsburgh 13, Pennsylvania

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