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Related Concept Videos

Phosphorylation01:02

Phosphorylation

55.8K
The addition or removal of phosphate groups from proteins is the most common chemical modification that regulates cellular processes. These modifications can affect the structure, activity, stability, and localization of proteins within cells as well as their interactions with other proteins.
During phosphorylation, protein kinases transfer the terminal phosphate group of ATP to specific amino acid side chains of substrate proteins. Serine, threonine, and tyrosine are the most commonly...
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Phosphorylation01:02

Phosphorylation

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8.1K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

7.6K
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom...
7.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.9K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.9K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

3.1K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
3.1K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

4.5K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
4.5K

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Updated: Apr 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Phosphonate–phosphinate rearrangement.

Renzhe Qian, Alexander Roller, Friedrich Hammerschmidt

    The Journal of Organic Chemistry
    |December 20, 2014
    PubMed
    Summary
    This summary is machine-generated.

    Lithium tetramethylpiperidide (LiTMP) and sec-butyllithium (s-BuLi) mediate distinct rearrangements in N-Boc-phosphoramidates. These reactions reveal new pathways for synthesizing functionalized phosphonamidates and α-aminophosphonates.

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    Area of Science:

    • Organic Chemistry
    • Organophosphorus Chemistry
    • Stereoselective Synthesis

    Background:

    • N-Boc-phosphoramidates are versatile intermediates in organic synthesis.
    • Understanding the reactivity of these compounds under different lithiation conditions is crucial for developing new synthetic methodologies.

    Purpose of the Study:

    • To investigate the regioselectivity and stereoselectivity of LiTMP and s-BuLi mediated deprotonation of N-Boc-phosphoramidates.
    • To explore the subsequent rearrangements, including phosphate–phosphonate and phosphonate–phosphinate rearrangements.

    Main Methods:

    • Deprotonation of dimethyl N-Boc-phosphoramidates using LiTMP and s-BuLi.
    • Analysis of reaction products using techniques such as NMR spectroscopy to determine structure and stereochemistry.
    • Investigation of reaction mechanisms, including isomerization and rearrangement pathways.

    Main Results:

    • LiTMP selectively metalates the CH3O group, forming oxymethyllithiums that isomerize to hydroxymethylphosphonamidates.
    • s-BuLi preferentially forms N-Boc α-aminophosphonates from specific phosphoramidates.
    • s-BuLi induces phosphonate–phosphinate rearrangements, with stereochemical outcomes dependent on the substrate and intermediate formation.

    Conclusions:

    • The choice of base (LiTMP vs. s-BuLi) dictates the site of deprotonation and the subsequent reaction pathway.
    • Stereoselective synthesis of functionalized phosphonamidates and α-aminophosphonates is achievable through controlled lithiation and rearrangement.
    • The study elucidates novel rearrangement mechanisms involving organolithium intermediates.