Borates and phosphates of hexahydromuellitol and isomuellitol

Abstract

Hexahydromuellitol and isomuellitol are derivatives of a natural product (muellitol), and contain hydroxy groups in their structures which should allow for the formation of 'cage' compounds. They were each dissolved in a standard borate solution, and the pH values were measured to determine if complexes of the tridentate type were formed. Hexahydromuellitol caused the pH value of the solution to be depressed considerably, but isomuellitol had no significant effect. Plots of the change in pH value against time showed that a tridentate borate of hexahydromuellitol was formed but not of isomuellitol.

Orthophosphates were prepared from both compounds to verify the assigned conformations. The mono-and the di-orthophosphates of hexahydromuellitol were obtained, as was the orthophosphate of isomuellitol.