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Reductive coupling of 4,5-ethylenedithio-1,3-diselenol-2-one; Bis(ethylenedithiotetraselenafulvalene)

SyntheticPage 421
DOI: 10.1039/SP421
Submitted May 28, 2010, published Jun 01, 2010
Nikola Paul Chmel (
A contribution from Scott group, Warwick University

			Reaction Scheme: <IMG src="/images/empty.gif">Reductive coupling of&nbsp;<SPAN id=csm1288162547415 class=csm-chemical-name title=4,5-ethylenedithio-1,3-diselenol-2-one>4,5-ethylenedithio-1,3-diselenol-2-one</SPAN><IMG src="/images/empty.gif">

Chemicals Used

4,5-ethylenedithio-1,3-diselenol-2-one synthesis

triethyl phosphite

toluene (refluxed over potassium, degassed)


Triethyl phosphite (10 ml) was added dropwise over 15 min to a solution of 4,5-ethylenedithio-1,3-diselenol-2-one (0.3 g, 0.99 mmol) in dry toluene (30 ml) under argon. The mixture was heated to reflux for 2 h and then allowed to cool. The product was collected by filtration and recrystallised from hot anhydrous carbon disulfide under argon (CAUTION - CS2 has a very low flash point and is highly inflammable). Yield 0.15 g (52%).

Author's Comments

BETS is really insoluble - CS2 was the best solvent we found for recrystallisation, it also dissolves sparingly in chloroform.

This procedure has been published in outline by Kato et al. and Courcet et al., to our knowledge however this is the first detailed synthetic procedure for this reaction. The coupling procedure was adapted from Imakubo et al.


Elemental analysis found (calculated for C10H8S4Se4) %: C 21.10 (20.99), H 1.20 (1.41)

1H NMR (400 MHz, 298K, CDCl3) δH 1.56 (s, 8H, CH2)

13C NMR, - no data obtained even on 700MHz and 16k scans - due to very low solubility

Lead Reference

R. Kato, H. Kobayashi and A. Kobayashi, Synth. Met., 1991, 42, 2093-2096.

Other References

T. Courcet, I. Malfant, K. Pokhodnia and P. Cassoux, New J. Chem., 1998, 22, 585-589.

T. Imakubo, M. Kibune, H. Yoshino, T. Shirahata and K. Yoza, J. Mater. Chem., 2006, 16, 4110-4116.

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Get structure file (.cdx, .sk2, .mol)

Keywords: alkenes, BEDT-TSeF, BEDT-TSF, BETS, heterocyclic compounds

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  • Guest PramodJun 14 2013 10:45AMTriethyl phosphate

    In this scheme it is mentioned P(OEt)3 but in experimental it is written Triethyl phosphate. what is the real reagent used? Phosphite or phosphate.

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