NEW PRECURSORS FOR PREPARING ORGANIC CONDUCTING MATERIALS - SYNTHESISOF YDROXYMETHYLBIS(ETHYLENEDITHIO)TETRATHIAFULVALENE, AND THE RING EXPANSION OF A CYCLIC SULFATE ESTER

The chiral hydroxymethyl-substituted derivative of bis(ethylenedithio) tetrathiafulvalene, has been synthesized from D-mannitol via the cycli c sulfate ester of (2R)-3-(2-methoxyethoxymethoxy)propane-1,2-diol. Th e latter substance slowly decomposes at 45 degrees C and should be use d when freshly prepared. In contrast, the cyclic sulfate ester of (2R) -3-benzoyloxypropane-1,2-diol containing a five-membered ring, undergo es clean rearrangement at room temperature to the cyclic sulfate ester of 2-benzoyloxypropane 1,3-diol, containing a six-membered ring.