Journal of Flow Chemistry
Volume/Issue:
Volume 3: Issue 4
Flow Synthesis of Symmetrical Di- and Trisulfides Using Phase-Transfer Catalysis
Authors:
Alastair Baker School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK

Search for other papers by Alastair Baker in
Current site
Google Scholar
PubMed Close
,
Michael Graz Neem Biotech, Willowbrook Technical Units, Llandogo Road, St. Mellons, Cardiff, CF3 0EF, UK

Search for other papers by Michael Graz in
Current site
Google Scholar
PubMed Close
,
Robert Saunders Neem Biotech, Willowbrook Technical Units, Llandogo Road, St. Mellons, Cardiff, CF3 0EF, UK

Search for other papers by Robert Saunders in
Current site
Google Scholar
PubMed Close
,
Gareth J. S. Evans Neem Biotech, Willowbrook Technical Units, Llandogo Road, St. Mellons, Cardiff, CF3 0EF, UK

Search for other papers by Gareth J. S. Evans in
Current site
Google Scholar
PubMed Close
,
Sandra Kaul School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK

Search for other papers by Sandra Kaul in
Current site
Google Scholar
PubMed Close
, and
Thomas Wirth School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK

Search for other papers by Thomas Wirth in
Current site
Google Scholar
PubMed Close
Pages:
118–121
Online Publication Date:
13 Dec 2013
Publication Date:
13 Dec 2013
Article Category:
Research Article
DOI:
https://doi.org/10.1556/jfc-d-13-00013
Keywords:
flow chemistry; phase transfer catalysts; symmetrical disulfides; symmetrical trisulfides
Restricted access

Abstract

Using mild conditions and short reaction times, symmetrical disulfides have been synthesized in flow chemistry using phase transfer catalysts to facilitate the substitution of organohalides with disodium disulfide. Also, the synthesis of symmetrical trisulfides was possible using this procedure with an additional equivalent of sulfur.

  • 1. Joshi, A. V.; Bhusare, S.; Baidossi, M.; Qafisheh, N.; Sasson, Y. Tetrahedron Lett. 2005, 46, 3583–3585.

  • 2. (a) Singh, D.; Galetto, F. Z.; Soares, L. C.; Rodrigues, O. E. D.; Braga, A. L. Eur. J. Org. Chem. 2010, 2661–2665;

    (b)Thurow, S.; Pereira, V. A.; Martinez, D. M.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardão, E. J. Tetrahedron Lett. 2011, 52, 640–643.

    • Search Google Scholar
    • Export Citation

  • 3. Ghorbani-Choghamarani, A.; Nikoorazm, M.; Goudarziafshar, H.; Tahmasbi, B. Bull. Korean Chem. Soc. 2009, 30, 1388–1390.

  • 4. Ghorbani-Choghamarani, A.; Nikoorazm, M.; Goudarziafshar, H.; Shokr, A.; Almasi, H. J. Chem. Sci. 2011, 123, 453–457.

  • 5. (a) Lenardão, E. J.; Lara, R. G.; Silva, M. S.; Jacob, R. G.; Perin, G. Tetrahedron Lett. 2007, 48, 7668–7670;

    (b)Sengupta, D.; Basu, B. Tetrahedron Lett. 2013, 54, 2277–2281.

  • 6. Banfield, S. C.; Omori, A. T.; Leisch, H.; Hudlicky, T. J. Org. Chem. 2007, 72, 4989–4992.

  • 7. Chowdhury, S.; Samuel, P. M.; Das, I.; Roy, S. J. Chem. Soc., Chem. Commun. 1994, 1993–1994.

  • 8. Polshettiwar, V.; Nivsarkar, M.; Acharya, J.; Kaushik, M. P. Tetrahedron Lett. 2003, 44, 887–889.

  • 9. Dhar, P.; Chandrasekaran, S. J. Org. Chem. 1989, 54, 2998–3000.

  • 10. Sonavane, S. U.; Chidambaram, M.; Almog, J.; Sasson, Y. Tetrahedron Lett. 2007, 48, 6048–6050.

  • 11. Block, E.; Ahmad, S.; Catalfamo, J. L.; Jain, M. K.; Apitzcastro, R. J. Am. Chem. Soc. 1986, 108, 7045–7055.

  • 12. Wang, H. C.; Yang, J. H.; Hsieh, S. C.; Sheen, L. Y. J. Agric. Food Chem. 2010, 58, 7096–7103.

  • 13. Predmore, B. L.; Kondo, K.; Bhushan, S.; Zlatopolsky, M. A.; King, A. L.; Aragon, J. P.; Grinsfelder, D. B.; Condit, M. E.; Lefer, D. J. Am. J. Physiol. 2012, 302, H2410–H2418.

    • Search Google Scholar
    • Export Citation

  • 14. Kertmen, A.; Lach, S.; Rachon, J.; Witt, D. Synthesis 2009, 1459–1462.

  • 15. (a) Lach, S.; Sliwka-Kaszynska, M.; Witt, D. Synlett 2010, 2857–2860;

    (b)Demkowicz, S.; Rachon, J.; Witt, D. Synthesis 2008, 2033–2038.

  • 16. The micromixing device “Comet X-01,” available from Techno Applications Co., Ltd., 34-16-204, Hon, Denenchofu, Oota, Tokyo 145–0072, Japan, was used.

  • 17. Hutchings, M.; Ahmed-Omer, B.; Wirth, T. In Microreactors in Organic Chemistry and Catalysis, edition 2; Wirth, T., ed.; Wiley-VCH, Weinheim, 2013; 197–219.

    • Search Google Scholar
    • Export Citation

  • 18. Ahmed, B.; Barrow, D.; Wirth, T. Adv. Synth. Catal. 2006, 348, 1043–1048.

  • 19. Ahmed-Omer, B.; Barrow, D. A.; Wirth, T. Tetrahedron Lett. 2009, 50, 3352–3355.

  • Collapse
  • Expand
Cover Journal of Flow Chemistry
Journal of Flow Chemistry A Journal of the Flow Chemistry Society
Print ISSN:
2062-249X
Online ISSN:
2063-0212

To see the editorial board, please visit the website of Springer Nature.

Manuscript Submission: HERE

For subscription options, please visit the website of Springer Nature.

Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation		 2011
Volumes
per Year		 1
Issues
per Year		 4
Founder Áramlásos Kémiai Tudományos Társaság
Founder's
Address		 H-1031 Budapest, Hungary Záhony utca 7.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible
Publisher		 Chief Executive Officer, Akadémiai Kiadó
ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)

Monthly Content Usage

Abstract Views Full Text Views PDF Downloads
Apr 2024 26 0 0
May 2024 12 0 0
Jun 2024 20 0 1
Jul 2024 44 0 0
Aug 2024 78 0 0
Sep 2024 8 0 0
Oct 2024 11 0 0