Skip to main content
SpringerLink
Log in

Ultrasonic synthesis and crystal structure analysis of two trimethylsilyloxy-substituted bicyclo[2.2.2]octene derivatives

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

Abstract

The compounds: 11-trimethylsilyloxy-1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone and 4-benzyl-8-trimethylsilyloxy-4-aza-tricyclo[5.2.2.0]undec-8-ene-3,5-dione were synthesized by the Diels–Alder [4 π s  + 2 π s ] cycloaddition reaction of 2-(trimethylsilyloxy)-1,3-cyclohexadiene with naphthaquinone and N-benzylmaleimide under ultrasonic conditions. The crystal structure analysis was done using single crystal X-ray diffraction method. In both the compounds, the trimethylsilyloxy- and naphthaquinone/ N-benzylmaleimide moieties are endo- to the bicyclic ring.

The synthesis of two novel trimethylsilyloxy- substituted bicyclo[2.2.2]octene derivatives by employing ultrasonic reaction conditions is reported. The compounds have been characterized by single crystal X-ray studies.

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

Scheme 1
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5

Similar content being viewed by others

References

  1. Zhao F, Zhang S and Xi Z 2011 Chem. Commun. 47 4348

    Article  CAS  Google Scholar 

  2. (a) Paquette L A 1986 Chem. Rev. 86 733; (b) Bois M and Skrydstrup T 1995 Chem. Rev. 95 1253

    Google Scholar 

  3. Williams R V, Todime M M R, Enemark P, van der Helm D and Rizvi S K 1993 J. Org. Chem. 58 6740

    Article  CAS  Google Scholar 

  4. Mukherjee S and Corey E J 2010 Org. Lett. 12 632

    Article  CAS  Google Scholar 

  5. Hofmann M A, Nachbauer A, Bergstrager U and Regitz M 1999 Eur. J. Org. Chem. 1999 1041

    Article  Google Scholar 

  6. (a) Hariprasad S 2004 Resonance 80; (b) Langkopf E and Schinzer D 1995 Chem. Rev. 95 1375

  7. (a) Fleming I, Barbero A and Walter D 1997 Chem. Rev. 97 2063; (b) Birney D, Lim T K, Koh J H P, Pool B R and White J M 2002 J. Am. Chem. Soc. 124 5091

  8. (a) Goh Y W, Danczak S M, Lim T K and White J M 2006 J. Org. Chem. 72 2929; (b) Bats J W, Urschel B and Muller T 2008 Acta Crystalogr. E64 o2235

  9. (a) Begum N S, Girija C R, and Nagendrappa G 2004 Cryst. Eng Commun. 6 116; (b) Begum N S, Girija C R, Mallya N M and Nagendrappa G 2005 J. Mol. Struct. 751 127; (c) Begum N S, Vasundhara D E, Girija C R and Nagendrappa G 2008 Acta Crystalgr. C64 o423

  10. Nicolaou K C, Snyder S A, Montagnon T and Vassilikogiannakis G 2002 Angew. Chem. Int. Ed. 41 1668

    Article  CAS  Google Scholar 

  11. Buckle R N, Liu P Y, Roberts E W D and Burnell D J 1999 Tetrahedron 55 11455

    Article  CAS  Google Scholar 

  12. Gerard J 2002 Tetrahedron 58 5185

    Article  Google Scholar 

  13. Bruker 1998 SMART, SAINT-plus and SADBAS (Madison, Wisconsin, USA: Bruker AXS Inc)

    Google Scholar 

  14. Sheldrick G M 2008 Acta Crystalogr. A64 112

    Google Scholar 

  15. Farrugia L J and ORTEP-3 1999 J. Appl. Crystalogr. 32 837

    Article  CAS  Google Scholar 

  16. Nardelli M 1983 Acta Cryst. C39 1141

    CAS  Google Scholar 

  17. Srinivasa H T and HariPrasad S 2012 Org. Commun. 5(3) 128

    Google Scholar 

  18. Orhan B, Serkan Y, Mustafa O, Ozgur P and Yılmaz Y 2009 Acta Crystalogr. E65 o2208

    Google Scholar 

  19. Cremer D and Pople J A 1975 J. Am. Chem. Soc. 97 1354

    Article  CAS  Google Scholar 

  20. Reymond S and Cossy J 2008 Chem. Rev. 108 5359

    Article  CAS  Google Scholar 

  21. Pidaparthi R R, Junker C S, Welker M E, Day C S and Wright M W 2009 J. Org. Chem. 74 8290

    Article  CAS  Google Scholar 

Download references

Acknowledgements

HP and NSB are thankful to the University Grants Commission (UGC) and the Department of Science and Technology (DST), New Delhi, India for the financial assistance.

Author information

Authors and Affiliations

  1. Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B R Ambedkar Street, Bangalore, 560 001, India

    H T SRINIVASA, H NAGARAJAIAH, S HARIPRASAD & NOOR SHAHINA BEGUM

  2. Department of Post Graduate Studies and Research in Physics, Tumkur University, Tumkur, 572 103, India

    B S PALAKSHAMURTHY

Authors
  1. H T SRINIVASA
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H NAGARAJAIAH
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B S PALAKSHAMURTHY
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S HARIPRASAD
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. NOOR SHAHINA BEGUM
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to NOOR SHAHINA BEGUM.

Rights and permissions

Reprints and permissions

About this article

Cite this article

SRINIVASA, H.T., NAGARAJAIAH, H., PALAKSHAMURTHY, B.S. et al. Ultrasonic synthesis and crystal structure analysis of two trimethylsilyloxy-substituted bicyclo[2.2.2]octene derivatives. J Chem Sci 125, 1079–1085 (2013). https://doi.org/10.1007/s12039-013-0480-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-013-0480-0

Keywords

Search

Navigation