ArticleThe Journal of organic chemistry2017
Lithium Diisopropylamide: Nonequilibrium Kinetics and Lessons Learned about Rate Limitation.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
17 citing papers in PubMed, 35 citations in OpenAlex.
- Article
- Potassium Hexamethyldisilazide (KHMDS): Solvent-Dependent Solution Structures.Journal of the American Chemical Society · 2024Article
- Carbon-Nitrogen Bond Formation Using Sodium Hexamethyldisilazide: Solvent-Dependent Reactivities and Mechanisms.Journal of the American Chemical Society · 2023Article
- Directed Lithiation of Protected 4-Chloropyrrolopyrimidine: Addition to Aldehydes and Ketones Aided by Bis(2-dimethylaminoethyl)ether.Molecules (Basel, Switzerland) · 2023Article
- Lithiated Oppolzer Enolates: Solution Structures, Mechanism of Alkylation, and Origin of Stereoselectivity.Journal of the American Chemical Society · 2022Article
- Diastereoselectivity is in the Details: Minor Changes Yield Major Improvements to the Synthesis of Bedaquiline.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Ketone Enolization with Sodium Hexamethyldisilazide: Solvent- and Substrate-DependentJournal of the American Chemical Society · 2021Article
- Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis byJournal of the American Chemical Society · 2021Article
- Article
- Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation.Journal of the American Chemical Society · 2019Article
- Sodium Diisopropylamide-Mediated Dehydrohalogenations: Influence of Primary- and Secondary-Shell Solvation.The Journal of organic chemistry · 2019Article
- Aryl Carbamates: Mechanisms of Orthosodiations and Snieckus-Fries Rearrangements.The Journal of organic chemistry · 2019Article
- Pseudophedrine-Derived Myers Enolates: Structures and Influence of Lithium Chloride on Reactivity and Mechanism.Journal of the American Chemical Society · 2019Article
- Case for Lithium Tetramethylpiperidide-Mediated Ortholithiations: Reactivity and Mechanisms.Journal of the American Chemical Society · 2018Article
- Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Arene Metalations.Journal of the American Chemical Society · 2017Article
- Lithium Hexamethyldisilazide-Mediated Enolization of Highly Substituted Aryl Ketones: Structural and Mechanistic Basis of the E/Z Selectivities.Journal of the American Chemical Society · 2017Article
- Evans Enolates: Structures and Mechanisms Underlying the Aldol Addition of Oxazolidinone-Derived Boron Enolates.The Journal of organic chemistry · 2017Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
The kinetics of lithium diisopropylamide (LDA) in tetrahydrofuran under nonequilibrium conditions are reviewed. These conditions correspond to a class of substrates in which the rates of LDA aggregation and solvation events are comparable to the rates at which various fleeting intermediates react with substrate. Substrates displaying these reactivities, by coincidence, happen to be those that react at tractable rates on laboratory time scales at -78 °C. In this strange region of nonlimiting behavior, rate-limiting steps are often poorly defined, sometimes involve deaggregation, and at other times include reaction with substrate. Changes in conditions routinely cause shifts in the rate-limiting steps, and autocatalysis is prevalent and can be acute. The studies are described in three distinct portions: (1) methods and strategies used to deconvolute complex reaction pathways, (2) the resulting conclusions about organolithium reaction mechanisms, and (3) perspectives on the concept of rate limitation reinforced by studies of LDA in tetrahydrofuran at -78 °C under nonequilibrium conditions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.