1,4‐Di‐<i>tert</i>‐butyl‐2,6‐bis(trimethylsilyl)silabenzol, das erste in Lösung bis – 100°C stabile Silabenzol

Märkl, Gottfried; Schlosser, W.

doi:10.1002/ange.19881000741

Cited by 23 publications

(3 citation statements)

References 20 publications

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“…The silabenzene, as well as its heavier analogues, has been a long‐standing synthetic attraction for many research groups,30 yet the isolation of the first stable sila‐aromatics was accomplished only a decade ago. Earlier, the closest approach to the synthesis of a silabenzene derivative was demonstrated by Märkl and Schlosser, who reported the generation and NMR observation of the 1,4‐di‐ tert ‐butyl‐2,6‐bis(trimethylsilyl)‐1‐silabenzene 31. However, the silabenzene generated by this method was stable only at temperatures below −100 °C; moreover, it was evidently coordinated by the nucleophilic solvent (THF), as shown by its high‐field 29 Si NMR resonance at δ =26.8 ppm.…”

Section: Species With Six π Electronsmentioning

confidence: 99%

Aromaticity of Group 14 Organometallics: Experimental Aspects

2007

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The long story of aromatic compounds has extended over almost two centuries, since the discovery by Faraday of "bicarburet of hydrogen", or C(6)H(6), now called benzene. Since then, the chemistry of aromatic compounds has been developed extensively; this is reflected in the synthesis of novel classes of aromatic derivatives including charged species, nonclassical (Möbius, three-dimensional, homo-, metalla-) aromatics, and fullerenes. The theory of aromaticity has also undergone a spectacular evolution since the first definition of aromaticity by Hückel; the classification of aromaticity now requires the consideration of versatile criteria: energetic, structural, magnetic, among others. In this Review, we discuss the current state of affairs in the chemistry of aromatic compounds of the heavier Group 14 elements, the latest experimental achievements, as well as future prospects in the field.

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Section: Species With Six π Electronsmentioning

confidence: 99%

Aromaticity of Group 14 Organometallics: Experimental Aspects

2007

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“…Trotz des lange bestehenden Interesses an Silabenzol und seinen schwereren Analoga30 gelang die Isolierung der ersten stabilen Silaarene erst vor einem Jahrzehnt. Zuvor hatten Märkl und Schlosser das 1,4‐Di‐ tert ‐butyl‐2,6‐bis(trimethylsilyl)‐1‐silabenzol hergestellt und NMR‐spektroskopisch beobachtet31 – allerdings war das so erhaltene Silabenzol‐Derivat nur bei Temperaturen unterhalb von −100 °C stabil; wie das Hochfeld‐ 29 Si‐NMR‐Signal bei δ =26.8 ppm belegte, war es zudem offenbar durch das nucleophile Lösungsmittel (THF) koordiniert.…”

Section: Spezies Mit Sechs π‐Elektronenunclassified

Aromatizität von metallorganischen Verbindungen mit Gruppe‐14‐Elementen: experimentelle Aspekte

Lee

Sekiguchi

2007

Angewandte Chemie

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Die Aromatizität ist eines der wegweisenden Konzepte in der Chemie, dessen Geschichte sich über fast zwei Jahrhunderte erstreckt, beginnend mit der Entdeckung des “Doppelt‐Kohlenwasserstoffs” (bicarburet of hydrogen), heute Benzol genannt, durch Faraday. Die seitherigen Fortschritte auf dem Gebiet der aromatischen Verbindungen sind erheblich, was sich in der Synthese neuartiger Klassen aromatischer Verbindungen widerspiegelt, darunter geladene Spezies, nichtklassische (Möbius‐, dreidimensionale, Homo‐, Metalla‐)Arene und Fullerene. Zugleich wurde die Theorie der Aromatizität stetig weiterentwickelt; die Abgrenzung der Aromatizität erfordert heute eine Abwägung vielfältiger Kriterien: energetischer, struktureller, magnetischer Kriterien usw. Im vorliegenden Aufsatz diskutieren wir den derzeitigen Forschungsstand auf dem Gebiet der aromatischen Verbindungen von schwereren Gruppe‐14‐Elementen und geben einen Ausblick auf die Zukunft dieses Gebiets.

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“…Märkl and Schlosser came to the closest and reported the generation and NMR observation of the 1,4-di-tert-butyl-2,6bis(trimethylsilyl)-1-silabenzene. 103 However, the major breakthrough was achieved when Tokitoh and coworkers synthesized stable silabenzene by introducing the sterically encumbered 2,4,6-tris[bis(trimethylsilyl)-methyl]phenyl substituent at the silicon atom. 104 Parallel to this, Ando et al reported the synthesis of 1,4-disila-(Dewar-benzene).…”

Section: Kekulémentioning

confidence: 99%

Preparation and Reactions of Compounds with Heavier Group 14 Elements in Low Oxidation States

Sen¹

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The work described in this dissertation has been carried out under the guidance and supervision of Prof. Dr. Dr. h. c. mult. Herbert W. Roesky at the Institut für Anorganische Chemie der Georg-August-Universität in Göttingen between November 2006 and September 2010.At first, I would like to express my gratitude to Prof. Herbert W. Roesky for giving an excellent working atmosphere, granting academic freedom and his continuous motivation to tackle the regular challenges in chemistry of group 14 elements. His enthusiasm for 'high quality results' and perseverance inspired me for not to give up till the end. His confidence that things will turn to work at the end definitely encouraged me to overcome a couple of experimental failures.

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1,4‐Di‐tert‐butyl‐2,6‐bis(trimethylsilyl)silabenzol, das erste in Lösung bis – 100°C stabile Silabenzol

Cited by 23 publications

References 20 publications

Aromaticity of Group 14 Organometallics: Experimental Aspects

Aromaticity of Group 14 Organometallics: Experimental Aspects

Aromatizität von metallorganischen Verbindungen mit Gruppe‐14‐Elementen: experimentelle Aspekte

Preparation and Reactions of Compounds with Heavier Group 14 Elements in Low Oxidation States

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