Authors: | Brieger, Lukas Schrimpf, Tobias Scheel, Rebecca Unkelbach, Christian Strohmann, Carsten |
Title: | Towards substrate-reagent interaction of Lochmann-Schlosser bases in THF: bridging THF hides potential reaction site of a chiral superbase |
Language (ISO): | en |
Abstract: | The metalation of N,N-dimethylaminomethylferrocene in THF by the superbasic mixture of nBuLi/KOtBu proceeds readily at low temperatures to afford a bimetallic Li2K2 aggregate containing ferrocenyl anions and tert-butoxide. Starting from an enantiomerically enriched ortho-lithiated aminomethylferrocene, an enantiomerically pure superbase can be prepared. The molecular compound exhibits superbasic behavior deprotonating N,N-dimethylbenzylamine in the α-position and is also capable of deprotonating toluene. Quantum chemical calculations provide insight into the role of the bridging THF molecule to the possible substrate–reagent interaction. In addition, a benzylpotassium alkoxide adduct gives a closer look into the corresponding reaction site of the Lochmann–Schlosser base that is reported herein. |
Subject Headings: | Alkali metals Chirality Lithium Potassium X-ray diffraction |
URI: | http://hdl.handle.net/2003/42272 http://dx.doi.org/10.17877/DE290R-24109 |
Issue Date: | 2022-09-13 |
Rights link: | https://creativecommons.org/licenses/by/4.0/ |
Appears in Collections: | Lehrstühle für Anorganische Chemie |
Files in This Item:
File | Description | Size | Format | |
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Chemistry A European J - 2022 - Brieger - Towards Substrate Reagent Interaction of Lochmann Schlosser Bases in THF .pdf | DNB | 4.04 MB | Adobe PDF | View/Open |
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