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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


IMPACT FACTOR 2018: 0.961

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1865-7117
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Volume 71, Issue 8

Issues

Single functionalization of fenestrindane and centrohexaindane at the molecular periphery

Jens Linke
  • Department of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
  • Other articles by this author:
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/ Dietmar Kuck
  • Corresponding author
  • Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
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Published Online: 2016-06-14 | DOI: https://doi.org/10.1515/znb-2016-0067

Abstract

The single functionalization of the parent centropolyindane hydrocarbons fenestrindane (2) and centrohexaindane (3) at the molecular arene periphery has been studied. The monoformylation of 2 and 3 using the Rieche method resulted in the corresponding aldehydes, 7 and 10, in 23% and 35% yield, respectively. The Friedel-Crafts acetylation of 2 furnished 2-acetylfenestrindane (8) in 53% yield, and the Baeyer-Villiger oxidation of 7 followed by hydrolysis resulted in the 2-hydroxyfenestrindane (9) in 72% yield. The results show that electrophilic attack at one of the eight or, respectively, even 12 equivalent positions of 2 and 3 is a viable method for the monofunctionalization of these polycyclic aromatic hydrocarbons.

This article offers supplementary material which is provided at the end of the article.

Keywords: convex-concave hydrocarbons; electrophilic aromatic substitution; fenestranes; polycyclic aromatic hydrocarbons; regioselectivity; tribenzotriquinacenes

References

  • [1]

    W. E. Barth, R. G. Lawton, J. Am. Chem. Soc. 1966, 88, 380.Google Scholar

  • [2]

    L. T. Scott, M. M. Hashemi, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1991, 113, 7082.Google Scholar

  • [3]

    L. T. Scott, M. M. Hashemi, M. S. Bratcher, J. Am. Chem. Soc. 1992, 114, 1920.Google Scholar

  • [4]

    V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106, 4868.Google Scholar

  • [5]

    A. Borchardt, A. Fuchicello, K. V. Kilway, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 1921.Google Scholar

  • [6]

    Y. T. Wu, J. S. Siegel, Chem. Rev. 2006, 106, 4843.Google Scholar

  • [7]

    H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878.Google Scholar

  • [8]

    T. Amaya, T. Hirao, Pure Appl. Chem. 2012, 84, 1089.Google Scholar

  • [9]

    S. Higashibayashi, H. Sakurai, Chem. Lett. 2011, 40, 122.Google Scholar

  • [10]

    L. T. Scott, Pure Appl. Chem. 1996, 68, 291.Google Scholar

  • [11]

    T. J. Sieders, E. L. Elliott, G. Grube, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 7804.Google Scholar

  • [12]

    A. Sygula, R. Sygula, F. R. Fronczek, P. W. Rabideau, J. Org. Chem. 2002, 67, 6487.Google Scholar

  • [13]

    S. Mizyed, P. E. Georghiou, M. Bancu, B. Cuadra, A. K. Rai, P. Cheng, L. T. Scott, J. Am. Chem. Soc. 2001, 123, 12770.Google Scholar

  • [14]

    P. E. Georghiou, A. H. Tran, S. Mizyed, M. Bancu, L. T. Scott, J. Org. Chem. 2005, 70, 6158.Google Scholar

  • [15]

    K. Kawasumi, Q. Zhang, Y. Segawa, L. T. Scott, K. Itami, Nature Chem. 2013, 5, 739.Google Scholar

  • [16]

    M. N. Eliseeva, L. T. Scott, J. Am. Chem. Soc. 2012, 134, 15169.Google Scholar

  • [17]

    A. de Meijere, B. Stulgies, K. Albrecht, K. Rauch, H. A. Wegner, H. Hopf, L. T. Scott, L. Eshdat, I Aprahamian, M. Rabinovitz, Pure Appl. Chem. 2006, 78, 813.Google Scholar

  • [18]

    B. Babu Shrestha, S. Karanjit, S. Higashibayashi, H. Sakurai, Pure Appl. Chem. 2014, 86, 747.Google Scholar

  • [19]

    S. Higashibayashi, S. Onogi, H. Kumar Srivastava, G. Narahari Sastry, Y. T. Wu, H. Sakurai, Angew. Chem. Int. Ed. 2013, 52, 7314.Google Scholar

  • [20]

    D. Josa, J. Rodríguez-Otero, E. M. Cabaleiro-Lago, L. A. Santos, T. C. Ramalho, J. Phys. Chem. A 2014, 118, 9521.Google Scholar

  • [21]

    V. Rajeshkumar, Y. T. Lee, M. C. Stuparu, Eur. J. Org. Chem. 2016, 36.Google Scholar

  • [22]

    J. Tellenbröker, Doctoral thesis, Bielefeld University, Bielefeld, 1999.Google Scholar

  • [23]

    J. Linke, Doctoral thesis, Bielefeld University, Bielefeld, 2015.Google Scholar

  • [24]

    D. Kuck, Chem. Rev. 2006, 106, 4885.Google Scholar

  • [25]

    D. Kuck, Top. Curr. Chem. 1998, 196, 167.Google Scholar

  • [26]

    D. Kuck, Angew. Chem., Int. Ed. Engl. 1984, 23, 508.Google Scholar

  • [27]

    D. Kuck, Pure Appl. Chem. 2006, 78, 749.Google Scholar

  • [28]

    G. Markopoulos, L. Henneicke, J. Shen, Y. Okamoto, P. Jones, H. Hopf, Angew. Chem. Int. Ed. 2012, 51, 12884.Google Scholar

  • [29]

    J. G. Brandenburg, S. Grimme, P. G. Jones, G. Markopoulos, H. Hopf, M. K. Cyranski, D. Kuck, Chem. Eur. J. 2013, 19, 9930.Google Scholar

  • [30]

    D. Kuck, H. Bögge, J. Am. Chem. Soc. 1986, 108, 8107.Google Scholar

  • [31]

    D. Kuck, Chem. Ber. 1994, 127, 409.Google Scholar

  • [32]

    D. Kuck, A. Schuster, Angew. Chem., Int. Ed. Engl. 1988, 27, 1192.Google Scholar

  • [33]

    D. Kuck, A. Schuster, B. Paisdor, D. Gestmann, J. Chem. Soc., Perkin Trans. 1 1995, 721.Google Scholar

  • [34]

    D. Kuck, A. Schuster, C. Fusco, M. Fiorentino, R. Curci, J. Am. Chem. Soc. 1994, 116, 2375.Google Scholar

  • [35]

    C. Fusco, M. Fiorentino, A. Dinoi, R. Curci, R. A. Krause, D. Kuck, J. Org. Chem. 1996, 61, 8681.Google Scholar

  • [36]

    J. Tellenbröker, D. Kuck, Angew. Chem. Int. Ed. 1999, 38, 919.Google Scholar

  • [37]

    D. Kuck, A. Schuster, R. A. Krause, J. Tellenbröker, C. P. Exner, M. Penk, H. Bögge, A. Müller, Tetrahedron. 2001, 57, 3587.Google Scholar

  • [38]

    J. Tellenbröker, D. Kuck, Eur. J. Org. Chem. 2001, 1483.Google Scholar

  • [39]

    J. Strübe, B. Neumann, H.-G. Stammler, D. Kuck, Chem. Eur. J. 2009, 15, 2256.Google Scholar

  • [40]

    J. Tellenbröker, D. Kuck, Beilstein J. Org. Chem. 2011, 7, 329.Google Scholar

  • [41]

    H. Langhals, M. Rauscher, J. Strübe, D. Kuck, J. Org. Chem. 2008, 73, 1113.Google Scholar

  • [42]

    D. Kuck, J. Linke, L. C. Teichmann, D. Barth, J. Tellenbröker, D. Gestmann, B. Neumann, H.-G. Stammler, H. Bögge, Phys. Chem. Chem. Phys. 2016, 18, 11722.Google Scholar

  • [43]

    T. Wang, Y. F. Zhang, Q. Q. Hou, W. R. Xu, X. P. Cao, H. F. Chow, D. Kuck, J. Org. Chem. 2013, 78, 1062.Google Scholar

  • [44]

    W. X. Niu, T. Wang, Q. Q. Hou, Z. Y. Li, X. P. Cao, D. Kuck, J. Org. Chem. 2010, 75, 6704.Google Scholar

  • [45]

    W. X. Niu, E. Q. Yang, Z. F. Shi, X. P. Cao, D. Kuck, J. Org. Chem. 2012, 77, 1422.Google Scholar

  • [46]

    T. Wang, Q. Q. Hou, Q. F. Teng, X. J. Yao, W. X. Niu, X. P. Cao, D. Kuck, Chem. Eur. J. 2010, 16, 12412.Google Scholar

  • [47]

    W. Greschner, B. Neumann, H.-G. Stammler, H. Gröger, D. Kuck, Angew. Chem. Int. Ed. 2015, 54, 13764.Google Scholar

  • [48]

    B. Bredenkötter, B. Neumann, H.-G. Stammler, D. Kuck, Eur. J. Org. Chem. 2014, 53.Google Scholar

  • [49]

    J. Tellenbröker, D. Barth, B. Neumann, H.-G. Stammler, D. Kuck, Org. Biomol. Chem. 2005, 3, 570.Google Scholar

  • [50]

    M. Harig, D. Kuck, Eur. J. Org. Chem. 2006, 1647.Google Scholar

  • [51]

    D. Kuck, T. Hackfort, B. Neumann, H.-G. Stammler, Pol. J. Chem. 2007, 81, 875.Google Scholar

  • [52]

    A. Rieche, H. Gross, E. Höft, Chem. Ber. 1960, 93, 88.Google Scholar

  • [53]

    D. Kuck, A. Schuster, R. A. Krause, J. Org. Chem. 1991, 56, 3472.Google Scholar

  • [54]

    D. Kuck, in Advances in Theoretically Interesting Molecules, Vol. 4 (Ed.: R. P. Thummel), JAI Press, Greenwich, London, 1998, chapter 3, pp. 81–155.Google Scholar

About the article

Received: 2016-03-18

Accepted: 2016-05-03

Published Online: 2016-06-14

Published in Print: 2016-08-01


Funding Source: Deutsche Forschungsgemeinschaft

Award identifier / Grant number: DFG, KU 663/16-1

The authors are grateful for the financial support of the Deutsche Forschungsgemeinschaft (DFG, KU 663/16-1).


Citation Information: Zeitschrift für Naturforschung B, Volume 71, Issue 8, Pages 897–904, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2016-0067.

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