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, no.21, pp.3173-3177, 1997 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 1997
  • Doi Number: 10.1039/a704364c
  • Title of Journal : JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  • Page Numbers: pp.3173-3177

Abstract

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.