The Addition of Di-t-butyl Glutarate to Ketones to Yield Hydroxy Diesters by Means of Lithium Amide. Influence of Metallic Cation. Conversion to Unsaturated Acids

1962 ◽  
Vol 27 (11) ◽  
pp. 4010-4015 ◽  
Author(s):  
W. H. Puterbaugh
Keyword(s):  
Lithium Amide ◽  
Metallic Cation

Factors in Aldol Condensations of Alkyl Acetates with Benzophenone and Reversals by Sodium Amide Versus Lithium Amide. Metallic Cation Effects1

1960 ◽  
Vol 25 (8) ◽  
pp. 1296-1302 ◽  
Author(s):  
CHARLES R. HAUSER ◽  
WILLIAM R. DUNNAVANT
Keyword(s):  
Lithium Amide ◽  
Metallic Cation ◽  
Alkyl Acetates ◽  
Amide Versus ◽  
Sodium Amide

scholarly journals Lithium-mediated Ferration of Fluoroarenes

2020 ◽  
Vol 74 (11) ◽  
pp. 866-870
Author(s):  
Lewis C. H. Maddock ◽  
Alan Kennedy ◽  
Eva Hevia
Keyword(s):  
Hydrogen Atom ◽  
Organometallic Chemistry ◽  
Room Temperature ◽  
Structural Elucidation ◽  
Side Reactions ◽  
Metal Base ◽  
Lithium Amide ◽  
Mixed Metal ◽  
Important Challenge

While fluoroaryl fragments are ubiquitous in many pharmaceuticals, the deprotonation of fluoroarenes using organolithium bases constitutes an important challenge in polar organometallic chemistry. This has been widely attributed to the low stability of the in situ generated aryl lithium intermediates that even at –78 °C can undergo unwanted side reactions. Herein, pairing lithium amide LiHMDS (HMDS = N{SiMe3}2) with FeII(HMDS)2 enables the selective deprotonation at room temperature of pentafluorobenzene and 1,3,5-trifluorobenzene via the mixed-metal base [(dioxane)LiFe(HMDS)3] (1) (dioxane = 1,4-dioxane). Structural elucidation of the organometallic intermediates [(dioxane)Li(HMDS)2Fe(ArF)] (ArF = C6F5, 2; 1,3,5-F3-C6H2, 3) prior electrophilic interception demonstrates that these deprotonations are actually ferrations, with Fe occupying the position previously filled by a hydrogen atom. Notwithstanding, the presence of lithium is essential for the reactions to take place as Fe II (HMDS)2 on its own is completely inert towards the metallation of these substrates. Interestingly 2 and 3 are thermally stable and they do not undergo benzyne formation via LiF elimination.

The Metalation and Addition Reactions of Allylbenzene and Propenylbenzene with Butyllithium and Lithium Amide

1957 ◽  
Vol 79 (21) ◽  
pp. 5809-5814 ◽  
Author(s):  
Harry F. Herbrandson ◽  
David S. Mooney
Keyword(s):  
Addition Reactions ◽  
Lithium Amide

scholarly journals Compositional flexibility in Li-N-H materials: implications for ammonia catalysis and hydrogen storage.

2021 ◽  
Author(s):  
Joshua Makepeace ◽  
Jake M Brittain ◽  
Alisha Sukhwani Manghnani ◽  
Claire Murray ◽  
Thomas J Wood ◽  
...  
Keyword(s):  
Energy Storage ◽  
Hydrogen Storage ◽  
Compositional Variation ◽  
Lithium Amide ◽  
Lithium Imide ◽  
Energy Storage Applications

Li-N-H materials, particularly lithium amide and lithium imide, have been explored for use in a variety of energy storage applications in recent years. Compositional variation within the parent lithium imide,...

Decomposition of Lithium Amide and Lithium Imide with and without Anion Promoter

2011 ◽  
Vol 50 (13) ◽  
pp. 8058-8064 ◽  
Author(s):  
Junqing Zhang ◽  
Yun Hang Hu
Keyword(s):  
Lithium Amide ◽  
Lithium Imide

Enantioselective deprotonation of two racemic cyclic carbonyl compounds by a chiral lithium amide

1986 ◽  
Vol 27 (5) ◽  
pp. 631-634 ◽  
Author(s):  
M.B. Eleveld ◽  
H. Hogeveen
Keyword(s):  
Carbonyl Compounds ◽  
Lithium Amide ◽  
Enantioselective Deprotonation

Scope and limitations of the catalytic asymmetric rearrangement of epoxides to allylic alcohols using chiral lithium amide bases/lithiated imidazoles

2005 ◽  
Vol 46 (48) ◽  
pp. 8315-8318 ◽  
Author(s):  
Sally J. Oxenford ◽  
Jonathan M. Wright ◽  
Peter O’Brien ◽  
Narendra Panday ◽  
Mark R. Shipton
Keyword(s):  
Allylic Alcohols ◽  
Lithium Amide ◽  
Catalytic Asymmetric

Application of Homochiral Lithium Amide Base Chemistry to a Thiane Oxide System

Synlett ◽  
1992 ◽  
Vol 1992 (03) ◽  
pp. 194-196 ◽  
Author(s):  
Paul J. Cox ◽  
Andrew Persad ◽  
Nigel S. Simpkins
Keyword(s):  
Oxide System ◽  
Lithium Amide

Enantioselective catalytic rearrangement of cyclohexene oxide with new homochiral bis-lithium amide bases

2004 ◽  
Vol 15 (7) ◽  
pp. 1069-1072 ◽  
Author(s):  
Olivier Equey ◽  
Alexandre Alexakis
Keyword(s):  
Cyclohexene Oxide ◽  
Lithium Amide
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