Organic Reaction Mechanisms 2008 E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Serie: Organic Reaction Mechanisms
• Sprache: Englisch

Seitenzahl: 919

Veröffentlichungsjahr: 2011

Beschreibung

This volume is the 44th in this classical series. In every volume relevant reaction mechanisms are featured in chapters entitled: * Reaction of Aldehydes and Ketones and their Derivatives * Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives * Oxidation and Reduction * Carbenes and Nitrenes * Nucleophilic Aromatic Substitution * Electrophilic Aromatic Substitution * Carbocations * Nucleophilic Aliphatic Substitution * Carbanions and Electrophilic Aliphatic Substitution * Elimination Reactions * Addition Reactions: Polar Addition * Addition Reactions: Cycloadditions * Molecular Rearrangements An experienced team of authors is compiling these reviews every year, so that the reader can rely on a continuing quality of selection and presentation. As a new service to the reader all reaction mechanisms leading to stereospecific products are highlighted. This reflects the needs of the organic synthetic community with leads to chiral reactions. Detailed author and subject indexes help the reader to find the information they are looking for. As a new service to the reader all mechanisms featuring 'Enantiospecific and diastereospecific' reactions are highlighted. This reflects the interest of synthetic organic chemists in such reactions and the pharmaceutical role of chiral molecules.

Leseprobe

Contents

1.Reactions of Aldehydes and Ketones and their Derivativesby A. C. Knipe

Formation and Reactions of Acetals and Related Species

Reactions of Glucosides and Nucleosides

Formation and Reactions of Nitrogen Derivatives

C–C Bond Formation and Fission: Aldol and Related Reactions

Other Addition Reactions

Enolization and Related Reactions

Oxidation and Reduction of Carbonyl Compounds

Other Reactions

2.Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives by C. T. Bedford

INTERMOLECULAR CATALYSIS AND REACTIONS

ASSOCIATION-PREFACED CATALYSIS

BIOLOGICALLY SIGNIFICANT REACTIONS

3.Oxidation and Reduction by K. K. Banerji

Oxidation by Metal Ions and Related Species

Oxidation by Compounds of Non-metaSSie Elements

Ozonolysis and Ozonation

Peracids and Peroxides

Photo-oxygenation and Singlet Oxygen

Triplet Oxygen and Autoxidation

Other Oxidations

Reduction by Complex Metal Hydrides

Hydrogenation

Transfer Hydrogenation

Other Reductions

4.Carbenes and Nitrenes by M. G. Moloney

Reviews

Structure and Reactivity

Generation

Metal-bound Carbenes

Carbenes as Reagents

Addition and Fragmentation

Insertion and Abstraction

Rearrangement

Nitrenes

NucIeophilic Carbenes

Silylenes and Germylenes

5.Nucleophilic Aromatic Substitution byM. R. Crampton

General

The SNAr Mechanism

Heterocyclic Systems

Meiseeheimer and Related Complexes

6.Electrophilic Aromatic Substitution by R. G. Coombes

General

Halogenation

Nitration

Alkylation, Acylation, and Related Reactions

Other Reactions

7.Carbocations by R. A. McClelland

Introduction

Alkyl and Cycloalkyl Carbenium Ions

Benzyl Cations

Quinone Methides

Benzhydryl, Trityl, and Fluoreeyl Cations

Carbocation Reactivity-Quantitative Studies

Oxygen- and Sulfur-stabilized Cations

Carboeations Containing Silicon and Other Group 4 Elements

Halogenated Carbocations

Carbocations Containing Other Heteroatoms and Metals

Allyl and Vinyl Cations

Aryl Cations

Arenium Ions

Nitrenium Ions

Aromatic Systems

Dications

Polycyclic Systems

Carbonium (Bridged) Ions

Carbocations in Biosynthesis

8.Nucleophilic Aliphatic Substitution by A. C. Knipe

Carbocation Reactions

SN Reactions Forming C–C Bonds

SN Reactions Forming C–Y Bonds

Intramolecular Substitution

Anchimeric Assistance

Necleophilic Attack at Elements Other than Carbon

Medium Effects

Micelles and Phase-transfer Catalysis

Structural Effects

Theoretical Studies

Miscellaneous Kinetic Studies

Other Studies

9.Carbanions and Electrophilic Aliphatic Substitution by M. L. Birsa

Carbanion Structure and Stability

Carbanion Reactions

Proton-transfer Reactions

Miscellaneous

Electrophilic Aliphatic Substitution

10.Elimination Reactions by M. L. Birsa

E1cB Mechanisms

E2 Mechanisms

Solvolytic Reactions

Pyrolytic Reactions

Elimination Reactions in Synthesis

Other Reactions

11.Addition Reactions: Polar Addition by P. Kočovský

Reviews

Electrophilic Additions

Nucleophilic Additions

12.Addition Reactions: Cycloaddition by N. Dennis

2 + 2-Cycloadditioe

2 + 3-Cycloaddition

2 + 4-Cycloaddition

Miscellaneous Cycloadditions

13.Molecular Rearrangements: Part 1. Pericyclic Molecular Rearrangements by S. K. Armstrong

[3,3]-Sigmatropic Rearrangements

[2,3]-Sigmatropic Rearrangements

Other [N,M]-Sigmatropic Rearrangements

[1,n]-Sigmatropic Rearrangements

Diradical and Carbene Rearrangements

Electrocyclic Rearrangements

Group Transfer Reactions

Tandem Pericyclic Rearrangements

14.Molecular Rearrangements: Part 2. Other Reactions by A. Brandi and M. Gensini

Aromatic Rearrangements

Ionic Rearrangements

Rearrangements Involving Organometallic Compounds

Rearrangements Involving Ring Opening

Isomerizations

Tautomerism

Radical Rearrangements

Author Index

Subject Index

This edition first published 2011

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Contributors

S. K. ARMSTRONGFormerly at the Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, UKK. K. BANERJIIndra-Kripa, A-80 Saraswati Nagar, Jodhpur 342005, IndiaC. T. BEDFORDDepartment of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UKM. L. BIRSAFaculty of Chemistry, “Al. I. Cuza” University of Iasi, Bd. Carol I, 11, Iasi 700506, RomaniaA. BRANDIDipartimento di Chimica Organica “U. Schiff”, Universita’ degli Studi di Firenze-Polo Scientifico, Via della Lastruccia 13 1-50019 Sesto Fiorentino (Fl), ItalyR. G. COOMBESDepartment of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UKM. R. CRAMPTONDepartment of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UKN. DENNIS3 Camphorlaurel Court, Stretton, Brisbane, Queensland 4116, AustraliaM. GENSINIMenarini Ricerche S.p.A., Via Sette Santi, 3, 50131 Florence, ItalyA. C. KNIPEFaculty of Life and Health Sciences, University of Ulster, Coleraine, Northern IrelandP. KOČOVSKÝDepartment of Chemistry, The Joseph Black Building, The University of Glasgow, Glasgow G12 8QQ, UKR. A. McCLELLANDDepartment of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario, M5S 1A1, CanadaM. G. MOLONEYDepartment of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK

Preface

The present volume, the forty-fourth in the series, surveys research on organic reaction mechanisms described in the available literature dated 2008. In order to limit the size of the volume, it is necessary to exclude or restrict overlap with other publications which review specialist areas (e.g. photochemical reactions, biosynthesis, enzymology, electrochemistry, organometallic chemistry, surface chemistry and heterogeneous catalysis). In order to minimize duplication, while ensuring a comprehensive coverage, the editor conducts a survey of all relevant literature and allocates publications to appropriate chapters. While a particular reference may be allocated to more than one chapter, it is assumed that readers will be aware of the alternative chapters to which a borderline topic of interest may have been preferentially assigned.

In view of the considerable interest in application of stereoselective reactions to organic synthesis, we now provide indication, in the margin, of reactions which occur with significant diastereomeric or enantiomeric excess (de or ee).

Please note that the editor has written two chapters for this volume and Dr. M. G. Moloney has kindly contributed as a guest author. These and other steps are aimed to relieve pressure on continuing authors and thereby reduce progressively the delay between title year and publication date. As a consequence, we expect to publish several ORM volumes at nine-month intervals until our optimum production schedule is regained.

I wish to thank the production staff of John Wiley and Sons and the team of experienced contributors for their efforts to ensure that the review standards of this series are sustained.

A. C. K.