Combining Neopentyllithium with Potassium tert-Butoxide: Formation of an Alkane-Soluble Lochmann-Schlosser Superbase

Publication type:
Journal article
Metadata:
Autoren
  • Philipp Benrath
  • Maximilian Kaiser
  • Thomas Limbach
  • Mihail Mondeshki
  • Jan Klett
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000383473600068&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/anie.201602792
eISSN
1521-3773
Externe Identifier
  • Clarivate Analytics Document Solution ID: DW2LJ
  • PubMed Identifier: 27392232
ISSN
1433-7851
Ausgabe der Veröffentlichung
36
Zeitschrift
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Schlüsselwörter
  • alkali metals
  • alkoxy groups
  • carbanions
  • lithium
  • superbases
Paginierung
10886 - 10889
Datum der Veröffentlichung
2016
Status
Published
Titel
Combining Neopentyllithium with Potassium <i>tert</i>-Butoxide: Formation of an Alkane-Soluble Lochmann-Schlosser Superbase
Sub types
  • Article
Ausgabe der Zeitschrift
55

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<jats:title>Abstract</jats:title><jats:p>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 <jats:italic>tert</jats:italic>‐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/<jats:italic>tert</jats:italic>‐butoxy aggregates of varying compositions Li<jats:sub><jats:italic>x</jats:italic></jats:sub>K<jats:sub><jats:italic>y</jats:italic></jats:sub>Np<jats:sub><jats:italic>z</jats:italic></jats:sub>(O<jats:italic>t</jats:italic>Bu)<jats:sub><jats:italic>x</jats:italic>+<jats:italic>y</jats:italic>−<jats:italic>z</jats:italic></jats:sub>.</jats:p>
Autoren
  • Philipp Benrath
  • Maximilian Kaiser
  • Thomas Limbach
  • Mihail Mondeshki
  • Jan Klett
DOI
10.1002/anie.201602792
eISSN
1521-3773
ISSN
1433-7851
Ausgabe der Veröffentlichung
36
Zeitschrift
Angewandte Chemie International Edition
Sprache
en
Online publication date
2016
Paginierung
10886 - 10889
Datum der Veröffentlichung
2016
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/anie.201602792
Datum der Datenerfassung
2023
Titel
Combining Neopentyllithium with Potassium <i>tert</i>‐Butoxide: Formation of an Alkane‐Soluble Lochmann–Schlosser Superbase
Ausgabe der Zeitschrift
55

Data source: Crossref

Abstract
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 .
Addresses
  • Institut für Anorganische Chemie und Analytische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Autoren
  • Philipp Benrath
  • Maximilian Kaiser
  • Thomas Limbach
  • Mihail Mondeshki
  • Jan Klett
DOI
10.1002/anie.201602792
eISSN
1521-3773
Externe Identifier
  • PubMed Identifier: 27392232
Funding acknowledgements
  • University of Mainz:
Open access
false
ISSN
1433-7851
Ausgabe der Veröffentlichung
36
Zeitschrift
Angewandte Chemie (International ed. in English)
Sprache
eng
Medium
Print-Electronic
Online publication date
2016
Paginierung
10886 - 10889
Datum der Veröffentlichung
2016
Status
Published
Datum der Datenerfassung
2016
Titel
Combining Neopentyllithium with Potassium tert-Butoxide: Formation of an Alkane-Soluble Lochmann-Schlosser Superbase.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
55

Data source: Europe PubMed Central

Abstract
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 .
Autoren
  • Philipp Benrath
  • Maximilian Kaiser
  • Thomas Limbach
  • Mihail Mondeshki
  • Jan Klett
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/27392232
DOI
10.1002/anie.201602792
eISSN
1521-3773
Ausgabe der Veröffentlichung
36
Zeitschrift
Angew Chem Int Ed Engl
Schlüsselwörter
  • alkali metals
  • alkoxy groups
  • carbanions
  • lithium
  • superbases
Sprache
eng
Country
Germany
Paginierung
10886 - 10889
Datum der Veröffentlichung
2016
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2018
Titel
Combining Neopentyllithium with Potassium tert-Butoxide: Formation of an Alkane-Soluble Lochmann-Schlosser Superbase.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
55

Data source: PubMed

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