Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Lamm J-H, Niermeier P, Körte LA, Neumann B, Stammler H-G, Mitzel NW (2018)
SYNTHESIS-STUTTGART 50(10): 2009-2018.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9 H )-one was reacted with ethynylmagnesium bromide in the presence of CeCl (3) ; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.
Stichworte
anthracenes; alkynes; rigid organic frameworks; cross-coupling; reactions; solid-state structures
Erscheinungsjahr
2018
Zeitschriftentitel
SYNTHESIS-STUTTGART
Band
50
Ausgabe
10
Seite(n)
2009-2018
ISSN
0039-7881
eISSN
1437-210X
Page URI
https://pub.uni-bielefeld.de/record/2920324

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Lamm J-H, Niermeier P, Körte LA, Neumann B, Stammler H-G, Mitzel NW. Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks. SYNTHESIS-STUTTGART. 2018;50(10):2009-2018.
Lamm, J. - H., Niermeier, P., Körte, L. A., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2018). Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks. SYNTHESIS-STUTTGART, 50(10), 2009-2018. doi:10.1055/s-0036-1591925
Lamm, J. - H., Niermeier, P., Körte, L. A., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2018). Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks. SYNTHESIS-STUTTGART 50, 2009-2018.
Lamm, J.-H., et al., 2018. Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks. SYNTHESIS-STUTTGART, 50(10), p 2009-2018.
J.-H. Lamm, et al., “Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks”, SYNTHESIS-STUTTGART, vol. 50, 2018, pp. 2009-2018.
Lamm, J.-H., Niermeier, P., Körte, L.A., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks. SYNTHESIS-STUTTGART. 50, 2009-2018 (2018).
Lamm, Jan-Hendrik, Niermeier, Philipp, Körte, Leif Arne, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks”. SYNTHESIS-STUTTGART 50.10 (2018): 2009-2018.