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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π bonding...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.

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Related Experiment Video

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Carbohydrate functionalization using cationic iron carbonyl complexes.

Anders Bergh1, Henrik Gradén, Núria Parera Pera

  • 1Organic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, Göteborg, Sweden.

Carbohydrate Research
|May 13, 2008
PubMed
Summary

Researchers derivatized methyl beta-D-galactopyranosides at the 3-OH position using cationic iron carbonyl cyclohexadiene complexes. This yielded galactosides with novel aromatic or cyclohexadienoic functionalities for diverse applications.

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Area of Science:

  • Organometallic Chemistry
  • Carbohydrate Chemistry

Background:

  • Methyl beta-D-galactopyranosides are important carbohydrate building blocks.
  • Derivatization of the 3-OH position is crucial for modifying carbohydrate properties.

Purpose of the Study:

  • To explore the use of cationic iron carbonyl cyclohexadiene complexes for derivatizing methyl beta-D-galactopyranosides.
  • To synthesize galactosides with aromatic or cyclohexadienoic functionalities at the 3-OH position.

Main Methods:

  • Employing cationic iron carbonyl cyclohexadiene complexes.
  • Utilizing two distinct derivatization approaches.
  • Working with both unprotected and protected methyl beta-D-galactopyranosides.

Main Results:

  • Successful derivatization of the 3-OH position was achieved.
  • Access to galactopyranosides featuring aromatic or cyclohexadienoic groups was established.
  • The methodology proved effective for both protected and unprotected substrates.

Conclusions:

  • Cationic iron carbonyl cyclohexadiene complexes offer a versatile route for modifying carbohydrate structures.
  • The developed methods provide access to novel functionalized galactosides.