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

Fabien Leurquin, Turan Ozturk, Melanie Pilkington, John D. Wallis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

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°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.

Original languageEnglish
Pages (from-to)3173-3177
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number21
DOIs
Publication statusPublished - 7 Nov 1997
Externally publishedYes

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