Syntheses and Structures of 1,8,13,16-Substituted Triptycenes

Schwartzen A, Rovers M, Neumann B, Stammler H-G, Mitzel NW (2018)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2018(38): 5323-5333.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
New triptycene derivatives have been synthesised based on the cycloaddition between 1,8-bis[(trifluoromethanesulfonyl)-oxy]anthracene as well as 1,8-bis[(trimethylsilyl)ethynyl]anthracene and p-benzoquinone. The resulting triptycenequinones were the key compounds for further functionalisation of the triptycene backbone, which were completely characterised by multinuclear NMR spectroscopy, mass spectrometry and X-ray diffraction experiments. The aim was to substitute the triptycene backbone in positions 1, 8, 13 and 16 to avoid the formation of mixtures of syn- and anti-isomers of trisubstituted triptycenes. Based on the ditriflate-substituted triptycenequinone triptycene 1,8,13,16-tetratriflate was synthesised and reacted with alkynyl compounds in cross-coupling reactions. In further experiments the alkynyl-substituted triptycene to quinone was directly reacted with lithiated trimethylsilylacetylene or was initially reduced, consequently functionalised with triflate groups and reacted in Sonogashira cross-coupling reactions. It was found that both reaction pathways generate the anti-substituted product in position 16 as main product.
Stichworte
Triptycenes; Cycloaddition; Triflate; Cross-coupling reactions; Solid-state structures
Erscheinungsjahr
2018
Zeitschriftentitel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Band
2018
Ausgabe
38
Seite(n)
5323-5333
ISSN
1434-193X
eISSN
1099-0690
Page URI
https://pub.uni-bielefeld.de/record/2931975

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Schwartzen A, Rovers M, Neumann B, Stammler H-G, Mitzel NW. Syntheses and Structures of 1,8,13,16-Substituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2018;2018(38):5323-5333.
Schwartzen, A., Rovers, M., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2018). Syntheses and Structures of 1,8,13,16-Substituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018(38), 5323-5333. doi:10.1002/ejoc.201800770
Schwartzen, A., Rovers, M., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2018). Syntheses and Structures of 1,8,13,16-Substituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2018, 5323-5333.
Schwartzen, A., et al., 2018. Syntheses and Structures of 1,8,13,16-Substituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018(38), p 5323-5333.
A. Schwartzen, et al., “Syntheses and Structures of 1,8,13,16-Substituted Triptycenes”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2018, 2018, pp. 5323-5333.
Schwartzen, A., Rovers, M., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Syntheses and Structures of 1,8,13,16-Substituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2018, 5323-5333 (2018).
Schwartzen, Anna, Rovers, Marla, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Syntheses and Structures of 1,8,13,16-Substituted Triptycenes”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2018.38 (2018): 5323-5333.