Skip to main content

Synthesis and Reactions of Pentiptycenes and Their Derivatives

  • Chapter
  • First Online:
Iptycenes Chemistry
  • 1157 Accesses

Abstract

Compared with the first synthesis of triptycene in 1942 [Bartlett et al. in J Am Chem Soc 64(11):2649–2653, 1942], it was not until 32 years later that Skvarche and Shalaev [Dokl Akad Nauk SSSR 216(1):110–112, 1974] first accomplished the synthesis of pentiptycene (2). As shown in Scheme 3.1, pentiptycene 2 was synthesized in about 10 % total yield by a three-step route starting from 2-aminotriptycene 1. Similar to the way for the synthesis of triptycene, the Diels–Alder reaction between anthracene and benzyne was also the key process to pentiptycene.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Bartlett PD, Ryan MJ, Cohen SG (1942) Triptycene (9,10-o-benzenoanthracene). J Am Chem Soc 64(11):2649–2653

    Article  CAS  Google Scholar 

  2. Skvarche VR, Shalaev VK (1974) Aromatic-hydrocarbons: new aryn-2,3-dehydrotriptycene in reaction with anthracene. Dokl Akad Nauk SSSR 216(1):110–112

    Google Scholar 

  3. Hart H, Lai C, Nwokogu G, Shamouilian S, Teuerstein A, Zlotogorski C (1980) Bis-annelation of arenes with bis-aryne equivalents. J Am Chem Soc 102(21):6649–6651

    Article  CAS  Google Scholar 

  4. Hart H, Shamouilian S, Takehira Y (1981) Generalization of the triptycene concept. Use of diaryne equivalents in the synthesis of iptycenes. J Org Chem 46(22):4427–4432

    Article  CAS  Google Scholar 

  5. Hart H, Bashirhashemi A, Luo J, Meador MA (1986) Iptycenes-extended triptycenes. Tetrahedron 42(6):1641–1654

    Article  CAS  Google Scholar 

  6. Pei BJ, Chan WH, Lee AWM (2010) Oxadisilole fused triptycene and extended triptycene: precursors of triptycyne and extended triptycyne. J Org Chem 75(21):7332–7337

    Article  CAS  Google Scholar 

  7. Cadogan JIG, Harger MJP, Sharp JT (1971) Acylarylnitrosamines. Part III. Decomposition of 2,5-di-(N-nitrosoacetamido)-1,4-di-t-butylbenzene and related compounds. J Chem Soc B 602–607

    Google Scholar 

  8. Luo JM, Hart H (1987) New iptycenes using 2,3-naphtho[b]triptycene as a synthon. J Org Chem 52(16):3631–3636

    Article  CAS  Google Scholar 

  9. Zyryanov GV, Palacios MA, Anzenbacher P (2008) Simple molecule-based fluorescent sensors for vapor detection of TNT. Org Lett 10(17):3681–3684

    Article  CAS  Google Scholar 

  10. Clar E (1931) Über die konstitution des anthracens (zur kenntnis mehrkerniger aromatischer kohlenwasserstoffe und ihrer abkömmlinge, IX. Mitteil.). Ber 64(7):1676–1688

    Google Scholar 

  11. Theilacker W, Berger-Brose U, Beyer KH (1960) Untersuchungen in der triptycen-reihe, I. Synthese des triptycens und seiner 9- und 9,10-derivate. Chem Ber 93(7):1658–1681

    Article  CAS  Google Scholar 

  12. Hart H (1993) Iptycenes, cuppedophanes and cappedophanes. Pure Appl Chem 65(1):27–34

    Article  CAS  Google Scholar 

  13. Wiehe A, Senge MO, Kurreck H (1997) One-step synthesis of functionalized triptycene-quinones as acceptors for electron−transfer compounds. Liebigs Ann 1997(9):1951–1963

    Article  Google Scholar 

  14. Yang JS, Swager TM (1998) Porous shape persistent fluorescent polymer films: an approach to TNT sensory materials. J Am Chem Soc 120(21):5321–5322

    Article  CAS  Google Scholar 

  15. Yang JS, Swager TM (1998) Fluorescent porous polymer films as TNT chemosensors: electronic and structural effects. J Am Chem Soc 120(46):11864–11873

    Article  CAS  Google Scholar 

  16. Williams VE, Swager TM (2000) Iptycene-containing poly(arylene-ethynylene)s. Macromolecules 33(11):4069–4073

    Article  CAS  Google Scholar 

  17. Spyroudis S, Xanthopoulou N (2003) The reaction of triptycene haloquinones with alkoxides. An unusual route to pentiptycene quinones. Tetrahedron Lett 44(19):3767–3770

    Article  CAS  Google Scholar 

  18. Zhu XZ, Chen CF (2005) Iptycene quinones: synthesis and structure. J Org Chem 70(3):917–924

    Article  CAS  Google Scholar 

  19. Cao J, Lu HY, Chen CF (2009) Synthesis, structures, and properties of peripheral o-dimethoxy-substituted pentiptycene quinones and their o-quinone derivatives. Tetrahedron 65(39):8104–8112

    Article  CAS  Google Scholar 

  20. Yang JS, Ko CW (2006) Pentiptycene chemistry: new pentiptycene building blocks derived from pentiptycene quinones. J Org Chem 71(2):844–847

    Article  CAS  Google Scholar 

  21. Newman M, Boden H (1961) Notes: N-methylpyrrolidone as solvent for reaction of aryl halides with cuprous cyanide. J Org Chem 26(7):2525–2525

    Article  CAS  Google Scholar 

  22. Raap J, Nieuwenhuis S, Creemers A, Hexspoor S, Kragl U, Lugtenburg J (1999) Synthesis of isotopically labelled L-phenylalanine and L-tyrosine. Eur J Org Chem 1999(10):2609–2621

    Article  Google Scholar 

  23. Hegedus LS (1994) Organometallics in synthesis. Wiley, New York

    Google Scholar 

  24. Yang JS, Yan JL, Jin YX, Sun WT, Yang MC (2009) Synthesis of new halogenated pentiptycene building blocks. Org Lett 11(6):1429–1432

    Article  CAS  Google Scholar 

  25. Kundu SK, Tan WS, Yan JL, Yang JS (2010) Pentiptycene building blocks derived from nucleophilic aromatic substitution of pentiptycene triflates and halides. J Org Chem 75(13):4640–4643

    Article  CAS  Google Scholar 

  26. Hart H, Raju N, Meador MA, Ward DL (1983) Synthesis of heptiptycenes with face-to-face arene rings via a 2,3:6,7-anthradiyne equivalent. J Org Chem 48(23):4357–4360

    Article  CAS  Google Scholar 

  27. Pei BJ, Lee AWM (2010) Highly efficient synthesis of extended triptycenes via Diels−Alder cycloaddition in water under microwave radiation. Tetrahedron Lett 51(34):4519–4522

    Article  CAS  Google Scholar 

  28. Warrener RN (1971) Isolation of isobenzofuran, a stable but highly reactive molecule. J Am Chem Soc 93(9):2346–2348

    Article  CAS  Google Scholar 

  29. Warrener RN, Hammer BC, Russell RA (1981) Regiospecific cycloaddition of 1-substituted isobenzofurans to quinone acetals. J Chem Soc Chem Commun (18):942–943

    Google Scholar 

  30. Pei BJ, Chan WH, Lee AWM (2011) Anthracene capped isobenzofuran: a synthon for the preparations of iptycenes and iptycene quinones. Org Lett 13(7):1774–1777

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chuan-Feng Chen .

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Chen, CF., Ma, YX. (2013). Synthesis and Reactions of Pentiptycenes and Their Derivatives. In: Iptycenes Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32888-6_3

Download citation

Publish with us

Policies and ethics