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4. Sila-Peterson Reaction of Cyclic Silanides

Author

Kyri, Andreas W., primary, Schuh, Lukas, additional, Knoechl, Andreas, additional, Schalli, Michael, additional, Torvisco, Ana, additional, Fischer, Roland C., additional, Haas, Michael, additional, and Stueger, Harald, additional

Published
2020
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6. Reactivity of Cyclic Silenolates Revisited

Author

Haas, Michael, Leypold, Mario, Schuh, Lukas, Fischer, Roland, Torvisco, Ana, and Stueger, Harald

Abstract

The stable exocyclic silenolates 2a–c(2a, R = Mes; 2b, R = o-Tol; 2c, R = 1-Ad) were fully characterized by NMR and UV–vis spectroscopy. According to spectroscopic and structural features, 2a–care best described as acyl silyl anions (tautomeric structure I) in solution. This behavior is also reflected by the reaction of 2a,cwith MeI. Both alkylation reactions take place at the corresponding silicon atom and lead to the formation of the methylated structures 4a,bin nearly quantitative yields. Furthermore, the thermal stability of exocyclic silenolates 2a,cwas investigated. In the case of 2a, a thermally induced intramolecular sila-Peterson alkenation was observed at 60 °C. This transformation allowed straightforward access to 2-oxahexasilabicyclo[3.2.1]octan-8-ide 5as a structurally complex, bicyclic silicon framework. In contrast to that, heating of 2c, as an example of an alkyl-substituted silenolate, led to an unexpected degradation to uncharacterized polymers. However, we were able to isolate the 1-adamantyl-substituted, bicyclic compound 8, which is structurally closely related to 5, by the treatment of 1,4-dipotassium-1,4-bis(trimethylsilyl)cyclohexasilane with 1 equiv of 1-adamantoyl chloride. Again an intramolecular sila-Peterson alkenation is responsible for the formation of 8. The mechanism for this highly selective reaction sequence is outlined and supported by density functional theory (DFT) calculations, which highlight the thermodynamic driving force and the low activation barriers of this multistep transformation.

Published
2024
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11. Tetraacylgermanes: Highly Efficient Photoinitiators for Visible‐Light‐Induced Free‐Radical Polymerization

Author

Radebner, Judith, primary, Eibel, Anna, additional, Leypold, Mario, additional, Gorsche, Christian, additional, Schuh, Lukas, additional, Fischer, Roland, additional, Torvisco, Ana, additional, Neshchadin, Dmytro, additional, Geier, Roman, additional, Moszner, Norbert, additional, Liska, Robert, additional, Gescheidt, Georg, additional, Haas, Michael, additional, and Stueger, Harald, additional

Published
2017
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12. Tetraacylgermane: hochwirksame Photoinitiatoren für die radikalische Polymerisation mit sichtbarem Licht

Author

Radebner, Judith, primary, Eibel, Anna, additional, Leypold, Mario, additional, Gorsche, Christian, additional, Schuh, Lukas, additional, Fischer, Roland, additional, Torvisco, Ana, additional, Neshchadin, Dmytro, additional, Geier, Roman, additional, Moszner, Norbert, additional, Liska, Robert, additional, Gescheidt, Georg, additional, Haas, Michael, additional, and Stueger, Harald, additional

Published
2017
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15. Synthesis of Structurally Complex Silicon Frameworks through the First Sila-Aldol Reaction.

Author

Leypold M, Schuh L, Fischer R, Torvisco A, Flock M, Stueger H, and Haas M

Abstract

Herein, we report on the first sila-aldol reaction, which emphasizes the tight connection between silicon and carbon chemistry. This novel synthetic method provides straightforward access to 2-oxahexasilabicyclo[3.2.1]octan-8-ide, a structurally complex silicon framework, in quantitative yield. Its structure was confirmed by NMR spectroscopy and X-ray crystallography, and it displays a distinctive charge-transfer transition. The complete mechanism of this highly selective rearrangement cascade is outlined and supported by density functional theory (DFT) calculations, which highlight the thermodynamic driving force and the low activation barriers of this powerful silicon-carbon bond-forming strategy., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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16. Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization.

Author

Radebner J, Eibel A, Leypold M, Gorsche C, Schuh L, Fischer R, Torvisco A, Neshchadin D, Geier R, Moszner N, Liska R, Gescheidt G, Haas M, and Stueger H

Abstract

In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R] 4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge-based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one-pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time-resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo-DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long-wavelength visible-light photoinitiators for free-radical polymerization., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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