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TTF I. Addition of dimethyl acetylenedicarboxylate to ethylene trithiocarbonate; Dimethyl 1,3-dithiole-2-thione-4,5-dicarboxylate

SyntheticPage 277
DOI: 10.1039/SP277
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 I. Addition of dimethyl acetylenedicarboxylate to ethylene trithiocarbonate

Chemicals Used

ethylene trithiocarbonate (Aldrich),
dimethyl acetylenedicarboxylate (Aldrich)

Procedure

Dimethyl acetylenedicarboxylate (10.4 g, 0.073 mol) and ethylene trithiocarbonate (10 g, 0.073 mol) were dissolved in toluene (25 ml). Mixture was refluxed overnight at 150°C. Product precipitated upon cooling (water/ice bath), filtered without washing, dried in vacuo (Yield 16.8g). Concentration of the filtrate gave second crop (Yield 2.4g) Overall yield (19.2g, 89%)

Author's Comments

Has been performed several times with similar yields. Product used immediately in subsequent reaction.

Data

1H NMR (400MHz, Acetone-d6, 298K) 3.91 (s, CH3)

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: tetrathiafulvalene, TTF, addition, alkynes, esters, heterocyclic compounds, sulphides