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TTF II. Hydrolysis of dimethyl 1,3-dithiole-2-thione-4,5-dicarboxylate; 1,3-Dithiole-2-thione-4,5-dicarboxylic acid

SyntheticPage 278
DOI: 10.1039/SP278
Submitted Jun 05, 2008, published Jun 05, 2008
Nikola Paul Chmel (n.chmel@warwick.ac.uk)
A contribution from Scott group, Warwick University
Reaction Scheme: TTF II. Hydrolysis of dimethyl 1,3-dithiole-2-thione-4,5-dicarboxylate

Chemicals Used

dimethyl 1,3-dithiole-2-thione-4,5-dicarboxylate (see Page 277),
concentrated hydrochloric acid (Fisher),
glacial acetic acid (Fisher)

Procedure

Mixture of dimethyl 1,3-dithiole-2-thione-4,5-dicarboxylate (20g, 0.079mol), concentrated HCl (86ml), glacial acetic acid (40ml) in water (120ml) was refluxed at 170°C until all substrate dissolved (approx. 2 h). Product precipitated upon cooling (water/ice bath), filtered without washing, dried in vacuo. Filtrate was evaporated to dryness to obtain second crop. Total yield 17.8g

Author's Comments

Has been performed several times with similar yields. Product was used immediately in subsequent reaction, and this may be a good idea as it is slightly air sensitive.

Data

1H NMR (400MHz, Acetone-d6, 298K) 8.32 (s, COOH)

Lead Reference

L.R. Melby, H.D. Hartzler, W.A. Sheppard, J.Org. Chem. Vol. 39, No. 16, (1974) 2456-2458

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Keywords: TTF, tetrathiafulvalene, acid hydrolysis, nucleophilic, substitution, esters, heterocyclic compounds, sulphides