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Related Concept Videos

Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan biosynthesis begins in...

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3H-benzophosphepine complexes: versatile phosphinidene precursors.

Mark L G Borst1, Rosa E Bulo, Danièle J Gibney

  • 1Department of Chemistry, Faculty of Sciences, Vrije Universiteit, Amsterdam, The Netherlands.

Journal of the American Chemical Society
|December 1, 2005
PubMed
Summary

Researchers synthesized benzophosphepine complexes via hydrophosphination of 1,2-diethynylbenzene. These complexes act as phosphinidene precursors, with isomerization being the rate-determining step for their formation.

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Benzophosphepine complexes are valuable synthetic intermediates.
  • Hydrophosphination offers a route to complex phosphorus-containing heterocycles.

Purpose of the Study:

  • To detail the synthesis of benzophosphepine complexes.
  • To investigate their utility as phosphinidene precursors.
  • To elucidate the reaction mechanism.

Main Methods:

  • Two successive hydrophosphination reactions of 1,2-diethynylbenzene.
  • Use of various metal carbonyl complexes (W, Mo, Cr, Mn).
  • Kinetic and computational analyses.

Main Results:

  • Successful synthesis of diverse benzophosphepine complexes.
  • Identification of benzeno-1,4-diphosphinanes as side products.
  • Demonstration of phosphinidene generation at elevated temperatures (>55°C).
  • Phosphepine-phosphanorcaradiene isomerization identified as rate-determining.

Conclusions:

  • Benzophosphepine complexes are readily synthesized and serve as effective phosphinidene precursors.
  • The reaction pathway involves a key isomerization step.
  • Transient phosphinidenes can undergo further reactions, forming diphosphirene complexes.