Periodate Oxidation of Diol and Other Functional Groups

Periodate Oxidation of Diol and Other Functional Groups

Analytical and Structural Applications

1st Edition - January 1, 1970

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  • Author: Glenn Dryhurst
  • eBook ISBN: 9781483160801

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Description

Periodate Oxidation of Diol and Other Functional Groups: Analytical and Structural Applications deals with the chemistry of organic periodate oxidations with special reference to the study of carbohydrates, along with their analytical and structural applications. This book explores the mechanistic aspects of the periodate reaction; its historical development; the nature of the so-called anomalous reactions; and some of the synthetic uses of periodate oxidation. This book is comprised of seven chapters and opens with a historical background on periodate oxidation, followed by a discussion on the preparation and properties of periodates. The reader is then introduced to the mechanism of periodate oxidation, with particular reference to 1,2-diols and 1,2-hydroxycarbonyl compounds as well as 1,2-diketones, 1,2-aminoalcohols, and active methylene groups. The remaining chapters consider the structure of carbohydrates and related materials; anomalous periodate oxidations; the analytical aspects and applications of periodate oxidation; and a number of tested and generally well-tried analytical procedures such as the Fleury-Lange method, Malaprade method, ion exchange, and spectrophotometric and polarographic techniques. This monograph will be a useful resource for organic chemists and advanced undergraduate students of chemistry.

Table of Contents


  • Preface

    Introduction

    Chapter 1. History

    Literature Cited

    Chapter 2. Preparation and Properties of Periodates

    Preparation

    Solubility

    Stability of Aqueous Solutions

    Standard Potentials

    Ionization of Periodic Acid

    Structure of Periodates

    Literature Cited

    Chapter 3. Mechanism of Period ate Oxidation

    1,2-Diols

    Kinetics of Periodate Oxidation

    Further Evidence for a Cyclic Intermediate

    Alternative Mechanisms

    Conclusions

    1,2-Hydroxycarbonyl Compounds and 1,2-Diketones

    1,2-Aminoalcohols

    Active Methylene Groups

    Literature Cited

    Chapter 4. Anomalous Periodate Oxidations

    Overoxidation

    Sulfur-Containing Compounds

    Phenols

    Flavanols

    Amines

    Amino Acids

    Unsaturated Sugars

    Amino Sugars

    Proteins

    Oxidations at Elevated Temperature

    Oxidations in the Presence of Light

    Literature Cited

    Chapter 5. Periodate Oxidation in Structural Studies

    Structure Assignment Based on Periodate Oxidation Information

    Structure Assignment Based on Periodate Oxidation and Other Information

    Structure and End-Group Assay of Polysaccharides

    Nature of the Product of Periodate Oxidation

    Literature Cited

    Chapter 6. Analytical Methods

    Conditions of the Oxidation

    Solvent

    Oxidant

    Temperature

    Light

    Concentration of Reactants

    Duration of Reaction

    pH

    Buffer Composition

    Determination of Oxidant Consumption

    Müller-Friedberger Method

    Fleury-Lange Method

    Malaprade Method

    Discussion of Iodometric Methods

    Determination of α-Glycerophosphates in the Presence of ß-Glycerophosphates

    Other Methods for Periodate Determination

    Spectrophotometric

    Ion Exchange

    Polarographic

    H-Acid

    Determination of Glycerol

    Determination of Acid Produced

    Formic Acid

    Titration with Alkali

    Determination of Simple Sugars

    Influence of Overoxidation

    Procedure for Minimizing Overoxidation

    Procedure for Determination of Formic Acid and Formate Ester

    Potentiometric Titration

    Iodometric

    Removal of Formic Acid from Solution before Titration

    Gasometriç

    Spectrophotometric

    Mercuric Chloride

    Determination of Other Acids

    Glyoxylic Acid

    Carbonyl Acids

    Determination of Formaldehyde

    Mercuric Chloride

    Dimedone

    Chromotropic Acid

    Phenylhydrazine-Potassium Ferricyanide

    Acetylacetone

    Fluorimetric

    Determination of Acetaldehyde

    Iodometric

    Methyl Pentoses in the Presence of Hexoses

    Spectrophotometric

    Determination of Carbonyl Compounds with 2,4-Dinitrophenylhydrazine

    Determination of Ammonia and Amines

    Determination of Carbon Dioxide

    Recommended General Methods

    Oxidation of some Dihydroxy Aminoalkanes

    Oxidation of Maltotetraose

    Determination of Mixtures of Glycerol, Ethylene Glycol and 1,2-Propylene Glycol

    Oxidation on the Microgram Scale

    Periodate Oxidation of Borohydride-reduced Oligosaccharides

    Polarographic Determination of Ethylene Glycol and 1,2-Propylene Glycol

    Conclusions

    Literature Cited

    Chapter 7. Synthetic and Other Applications of Periodate Oxidations

    Literature Cited

    Author Index

    Subject Index

Product details

  • No. of pages: 204
  • Language: English
  • Copyright: © Pergamon 1970
  • Published: January 1, 1970
  • Imprint: Pergamon
  • eBook ISBN: 9781483160801

About the Author

Glenn Dryhurst

About the Editors

R. Belcher

D. M. W. Anderson

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