THE ACTION OF SODIUM IODIDE ON O-p-TOLUENE-SULPHONYL-1,4;3,6-DIANHYDRIDES OF D-MANNITOL, D-GLUCITOL, AND L-IDITOL

Abstract

In the displacement reaction with sodium iodide in acetic anhydride solution the rates of reaction of four isohexide tosyl esters were compared to that of an O-acetyl-O-tosylisosorbide recently described. The tosyloxy group in the latter compound was replaced rapidly and was therefore in the 5-endo-position, the compound being correctly named 2-O-acetyl-5-O-p-toluenesulphonyl-1,4;3,6-dianhydro-D-glucitol. The product of the reaction was isolated as a crystalline material, and was identified as 2-O-acetyl-5-deoxy-5-iodo-1,4;3,6-dianhydro-L-iditol.