Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons

Nierle J, Barth D, Kuck D (2004)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2004(4): 867-872.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
A previously overlooked hydrodehalogenation reaction occurring during the multiple Pd-0-catalysed C-C coupling reaction between pherylacetylene and hexaiodo- and hexabromobenzene was found to give pentakis(phenylethynyl)benzene ("pentatolane") as the major product, but no hexakis(phenylethynyl) benzene ("hexatolane") under conditions previously claimed to yield the latter hydrocarbon. As an alternative to a viable route to hexatolane described in the literature, an independent synthesis of this hydrocarbon through sixfold Sonogashira coupling of hexakis(ethynyl)benzene with iodobenzene has been developed. Some physical and spectroscopic properties of hexatolane and of the hitherto unknown pentatolane have been determined after thorough purification by HPLC. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Stichworte
palladium; ethynylbenzenes; alkynes; dehalogenation; C-C coupling
Erscheinungsjahr
2004
Zeitschriftentitel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Band
2004
Ausgabe
4
Seite(n)
867-872
ISSN
1434-193X
eISSN
1099-0690
Page URI
https://pub.uni-bielefeld.de/record/1608563

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Nierle J, Barth D, Kuck D. Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2004;2004(4):867-872.
Nierle, J., Barth, D., & Kuck, D. (2004). Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004(4), 867-872. doi:10.1002/ejoc.200300644
Nierle, J., Barth, D., and Kuck, D. (2004). Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2004, 867-872.
Nierle, J., Barth, D., & Kuck, D., 2004. Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004(4), p 867-872.
J. Nierle, D. Barth, and D. Kuck, “Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2004, 2004, pp. 867-872.
Nierle, J., Barth, D., Kuck, D.: Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2004, 867-872 (2004).
Nierle, J., Barth, Dieter, and Kuck, Dietmar. “Pentakis(phenylethynyl)benzene and hexakis(phenylethynyl)benzene: A revision concerning two far too similar prototype hydrocarbons”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2004.4 (2004): 867-872.