New precursors for preparing organic conducting materials: synthesis of (R)-hydroxymethylbis(ethylenedithio)tetrathiafulvalene, and the ring expansion of a cyclic sulfate ester

Leurquin F., Ozturk T., PILKINGTON M., WALLIS J.

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, sa.21, ss.3173-3177, 1997 (SCI-Expanded) identifier identifier

Özet

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