Periodate Oxidation of Diol and Other Functional Groups - 1st Edition - ISBN: 9780080068770, 9781483160801

Periodate Oxidation of Diol and Other Functional Groups

1st Edition

Analytical and Structural Applications

Authors: Glenn Dryhurst
Editors: R. Belcher D. M. W. Anderson
eBook ISBN: 9781483160801
Imprint: Pergamon
Published Date: 1st January 1970
Page Count: 204
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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

Details

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

About the Author

Glenn Dryhurst

About the Editor

R. Belcher

D. M. W. Anderson