TY - JOUR
T1 - New precursors for preparing organic conducting materials
T2 - Synthesis of (R)-hydroxymethylbis(ethylenedithio)tetrathiafulvalene, and the ring expansion of a cyclic sulfate ester
AU - Leurquin, Fabien
AU - Ozturk, Turan
AU - Pilkington, Melanie
AU - Wallis, John D.
PY - 1997/11/7
Y1 - 1997/11/7
N2 - 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°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.
AB - 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°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.
UR - http://www.scopus.com/inward/record.url?scp=33748816007&partnerID=8YFLogxK
U2 - 10.1039/a704364c
DO - 10.1039/a704364c
M3 - Article
AN - SCOPUS:33748816007
SN - 0300-922X
SP - 3173
EP - 3177
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 21
ER -