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Updated: Jul 2, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

An Isolable THF-Coordinated Dialkylgermanone

Kazuma Oshima¹, Ryo Kobayashi¹, Kengo Sakamoto¹

¹Department of Chemistry, Graduate School of Science, Tohoku University Aoba-ku, Sendai, 980-8578, Japan.

Chemistry, an Asian Journal

|February 21, 2024

Abstract:

A stable dialkylgermanone was generated by mixing a solid of the corresponding dialkylgermylene and gaseous N₂O. While the dialkylgermanone is marginally persistent in solution and gradually converts to its head-to-tail dimer at room temperature, the addition of THF to the dialkylgermanone provided an isolable THF-coordinated dialkylgermanone. The THF-coordinated dialkylgermanone reacts with H₂O, THF, and B(C₆F₅)₃ similar to the corresponding base-free two-coordinate dialkylsilanone. The dialkylgermanone undergoes deoxygenation in the presence of triphenylphosphine to provide the corresponding germylene and olefination upon treatment with phosphaylide Ph₃PCHPh to afford the corresponding Ge=C bond compound (germa-Wittig reaction).

Keywords:

Ge=O double bond Wittig reaction carbonyl groups ketones

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