Skip to main content
SpringerLink
Log in

Isolation and structures of some selenium and tellurium derivatives of 1, 4, 5, 8, 9, 12-hexabromododecahydrotriphenylene as co-crystals of triphenylene

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

The synthesis and characterization of low-valent organoselenium and tellurium derivatives of hexabromododecahydrotriphenylene has been attempted. The reaction of hexabromododecahydrotriphenylene with in situ generated disodium dichalcogenides (Na2E2; E = Se, Te) afforded insoluble chalcododecahydrotriphenylene derivatives, 20, 21 respectively. Attempted aromatization of 20 and 21 using DDQ (2, 3-dichloro-5, 6-dicyano-1,4-benzoquinone) as an oxidizing agent afforded the co-crystals. The hexaselenophenyl derivative, 22 and the hexaselenocyanate derivative 23 were synthesized by the reaction of in situ generated sodium arylselenolate/potassium selenocyanate with hexabromododecahydrotriphenylene, respectively. The compounds were characterized by common spectroscopic tools and a few by single crystal x-ray crystallographic studies.

Organoselenide 20 was synthesized by the reaction of 1, 4, 5, 8, 9, 12-hexabromododecahydrotriphenylene with in situ generated Na2Se2 at room temperature. Aromatization of 20 afforded compounds 24 and 26.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Chart 1
Scheme 1
Scheme 2
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6

Similar content being viewed by others

References

  1. Wu Y-T and Siegel J S 2006 Chem. Rev. 106 4843

  2. Tsefrikas V M and Scott L T 2006 Chem. Rev. 106 4868

  3. Van Dijk J T M, Hartwijk A, Bleeker A C, Lugtenburg J and Cornelisse J 1996 J. Org. Chem. 61 1136

  4. Sakurai H, Daiko T, Sakane H, Amaya T and Hirao T J. Am. Chem. Soc. 127 11580

  5. Sakurai H, Daiko T and Hirao T 2003 Science 301 1878

  6. Higashibayashi S and Sakurai H 2008 J. Am. Chem. Soc. 130 8592

  7. Tanaka H N T and Mikawa H 1982 Chem. Lett 1841

  8. Murschall R G H and Monch W 1982 Chem. Lett 727

  9. Murschall R, Gant H and Mönch W 1982 Solid State Commun. 42 787

  10. Li X, Zhu Y, Shao J, Wang B, Zhang S, Shao Y, Jin X, Yao X, Fang R and Shao X 2014 Angew. Chem. Int. Ed. 53 535

  11. Wei J, Jia X, Yu J, Shi X, Zhang C and Chen Z 2009 Chem. Commun. 4714

  12. Sheldrick G M SHELXS-97, Program for Crystal Structure Solution University of Göttingen, 1997

  13. Sheldrick G M SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen, 1997

  14. International Tables for X-ray Crystallography Vol 4 1974 (Birmingham: Kynoch Press)

  15. Wei J, Gao Y, Ma X, Jia X, Shi X and Chen Z 2010 Chem. Commun. 46 3738

  16. Selvakumar K, Singh H B, Goel N, Singh U P and Butcher R J 2011 Dalton Trans. 40 9858

  17. Panda A, Menon S C, Singh H B and Butcher R J 2001 J. Organomet. Chem. 62 87

  18. Müller J and Terfort A 2006 Inorg. Chim. Acta 359 4821

  19. Klemm L H, Hall E, Cousins L and Klopfenstein C E 1987 J. Heterocyclic Chem 24 1749

  20. Imamura K, Takimiya K, Otsubo T and Aso Y 1999 Chem. Commun. 1859

  21. Srivastava K, Shah P, Singh H B and Butcher R J 2011 Organometallics 30 534

  22. Ahmed F R and Trotter J 1963 Acta Cryst 16 503

  23. Zyss J, Ledoux-Rak I, Weiss H -C, Blasser D, Boesse R, Thallapally P K, Thalladi V R and Desiraju G R 2003 Chem. Matt. 15 3063

  24. Collings J C, Roscoe K P, Thomas R L, Batsanov A S, Stimson L M, Howard J A K and Marder T B 2001 New J. Chem. 25 1410

  25. Patra A, Wijsboom Y H, Leitus G and Bendikov M 2009 Organic Letters 11 1487

Download references

Acknowledgements

HBS is grateful to the Department of Science and Technology (DST), New Delhi (India), for generous funding. PRP is thankful to Department of Chemistry, IIT Bombay for a teaching assistantship.

Author information

Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India

    POONAM RAJESH PRASAD & HARKESH B SINGH

  2. Department of Chemistry, Howard University, Washington, DC, 20059, USA

    RAY J BUTCHER

Authors
  1. POONAM RAJESH PRASAD
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. HARKESH B SINGH
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. RAY J BUTCHER
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to HARKESH B SINGH.

Additional information

Supplementary Information

CCDC-1004393(3), CCDC-990989(3–24a), CCDC-99 0990(3–24b), CCDC-990991(3–24c), CCDC-990992 (3–26) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(PDF 105 KB)

(PDF 153 KB)

(PDF 128 KB)

(PDF 124 KB)

(PDF 144 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

PRASAD, P.R., SINGH, H.B. & BUTCHER, R.J. Isolation and structures of some selenium and tellurium derivatives of 1, 4, 5, 8, 9, 12-hexabromododecahydrotriphenylene as co-crystals of triphenylene. J Chem Sci 126, 1311–1321 (2014). https://doi.org/10.1007/s12039-014-0713-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-014-0713-x

Keywords

Search

Navigation