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RESEARCH PRODUCT
Combining Neopentyllithium with Potassium tert-Butoxide: Formation of an Alkane-Soluble Lochmann-Schlosser Superbase.
Philipp BenrathMaximilian KaiserThomas LimbachJan KlettMihail Mondeshkisubject
chemistry.chemical_classification010405 organic chemistryMetalationPotassiumSuperbasechemistry.chemical_elementGeneral Chemistry010402 general chemistryAlkali metal01 natural sciencesCatalysis0104 chemical scienceschemistry.chemical_compoundchemistryPotassium tert-butoxideAlkoxy groupOrganic chemistryReactivity (chemistry)Alkyldescription
Mixtures of alkyllithium and heavier alkali-metal alkoxides are often used to form alkyl compounds of heavier alkali metals, but these mixtures are also known for their high reactivity in deprotonative metalation reactions. These organometallic mixtures are often called LiC-KOR superbases, but despite many efforts their constitution remains unknown. Herein we present mixed alkali-metal alkyl/alkoxy compounds produced by reaction of neopentyllithium with potassium tert-butoxide. The key to success was the good solubility and temperature-stability of neopentyl alkali-metal compounds, leading to hexane-soluble mixtures, which allowed handling at ambient temperatures and isolation by crystallization. The compounds in solid state and in solution were identified by X-ray crystallography and NMR spectroscopy as mixtures of lithium/potassium neopentyl/tert-butoxy aggregates of varying compositions Lix Ky Npz (OtBu)x+y-z .
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-03-20 | Angewandte Chemie (International ed. in English) |