Organic Reaction Mechanisms 2007 E-Book

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

Seitenzahl: 874

Veröffentlichungsjahr: 2011

Beschreibung

Organic Reaction Mechanisms 2007, the 43rd annual volume in this highly successful and unique series, surveys research on organic reaction mechanisms described in the available literature dated 2007. The following classes of organic reaction mechanisms are comprehensively reviewed: * 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 * Polar Addition Reactions * Cycloaddition Reactions * Molecular Rearrangements An experienced team of authors compile these reviews every year, so that the reader can rely on a continuing quality of selection and presentation.

Leseprobe

CONTENTS

1. Reactions of Aldehydes and Ketones and their Derivatives by A. C. Knipe

Formation and Reactions of Acetals and Related Species

Reactions of Glucosides and Nucleosides

Reactions of Ketenes

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

References

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

INTERMOLECULAR CATALYSIS AND REACTIONS

Carboxylic Acids and their Derivatives

Phosphoric Acids and their Derivatives

Sulfonic Acids and their Derivatives

ASSOCIATION-PREFACED CATALYSIS

BIOLOGICALLY SIGNIFICANT REACTIONS

Enzymatic Catalysis

Intermolecular, Biomimetic and Model Reactions

References

3. Oxidation and Reduction by R. N. Mehrotra

Reviews and Accounts

Oxidation by Metal Ions and Related Species

Oxidation by Compounds of Non-metallic Elements

Ozonolysis and Ozonation

Peracids and Peroxides

Photo-oxygenation, Singlet Oxygen, and Superoxide

Triplet Oxygen and Autoxidation

Other Oxidations

Reduction by Complex Metal Hydrides

Other Reductions

Other Reactions

Synthesis Reactions

Acknowledgement

References

4. Carbenes and Nitrenes by E. Gras

Reviews

Generation, Structure, and Reactivity

Metal-bound Carbenes

Addition

Insertion

Rearrangement

Nucleophilic Carbenes - Carbenes as Organocatalysts

Nitrenes

Heavy-atom Carbene Analogues

References

5. Nucleophilic Aromatic Substitution by M. R. Crampton

General

The SNAr Mechanism

Heterocyclic Systems

Meisenheimer and Related Complexes

Benzyne and Related Intermediates

References

6. Electrophilic Aromatic Substitution by R. G. Coombes

General

Halogenation

Nitration

Alkylation, Acylation, and Related Reactions

Other Reactions

References

7. Carbocations by R. A. McClelland

Introduction

Alkyl and Cycloalkyl Carbenium Ions

Benzyl Cations

Quinone Methides

Benzhydryl, Trityl and Fluorenyl Cations

Carbocation Reactivity-Quantitative Studies

Oxygen and Sulfur Stabilized Cations

Carbocations Containing Silicon and Other Group 14 Elements

Halogenated Carbocations

Carbocations Containing Other Heteroatoms and Metals

Allylic Systems

Vinyl Cations

Aryl Cations

Arenium Ions

Nitrenium Ions

Aromatic Systems

Dications

Polycyclic Systems

Carbonium (Bridged) Ions

Carbocations in Biosynthesis

References

8. Nucleophilic Aliphatic Substitution by K. C. Westaway

SN Reactions Forming C-C Bonds

Allylic and Vinylic Substitutions

Reactions of Cyclic Ethers

Aziridines and Other Small Ring Substitutions

Studies Using Kinetic Isotope Effects

Nucleophilic Substitution on Elements Other than Carbon

Medium Effects/Solvent Effects

Micelles and Ion-pair Aggregates in Substitution Reactions

Structural Effects

Theoretical Studies

Gas-phase Substitution Reactions

Miscellaneous Kinetic and Product Studies

SN Reactions Producing Polymers

Acknowledgement

References

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

E2Mechanisms

Pyrolytic Reactions

Elimination Reactions in Synthesis

Other Reactions

References

11. Addition Reactions: Polar Addition by P. Kocovsky

Reviews

Electrophilic Additions

Nucleophilic Additions

References

12. Addition Reactions: Cycloaddition by N. Dennis

2 + 2-Cycloaddition

2 + 3-Cycloaddition

2 + 4-Cycloaddition

Miscellaneous Cycloadditions

References

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

[3,3]-Sigmatropic Rearrangements

[2,3]-Sigmatropic Rearrangements

Other [n,m]-Sigmatropic Rearrangements

[1,n]-Sigmatropic Rearrangements

Bergman and Related Diradical Rearrangements

Electrocyclic Rearrangements

Group Transfer Reactions

Tandem Pericyclic Rearrangements

References

14. Molecular Rearrangements: Part 2. Other Reactions by J. M. Coxon

Pericyclic Reactions

Named Reactions

Migration

Anionic Reactions and Rearrangements

Ring-closing and Ring-opening Reactions

Small-ring Chemsitry

Addition Reactions

Substitution Reactions

Oxidation

Carbene and Nitrene Reactions

Metathesis

Boranes

Silicon

Phosphorus

Metal-mediated Reactions

Radical, Biradical, and Radical-cation Reactions

Pyrolysis

Sugar Chemistry

References

Author Index

Subject Index

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Contributors

S.K. ARMSTRONGDepartment of Chemistry, University of Glasgow, Glasgow G12 8QQ, UKC.T. BEDFORDDepartment of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UKM.L. BIRSADepartment of Chemistry, Al I Cuza University of Iasi, Bd. Carol I, 11, Iasi 700506, RomaniaR.G. COOMBESDepartment of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UKJ.M. COXONDepartment of Chemistry, University of Canterbury, Christchurch, New ZealandM.R. CRAMPTONDepartment of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UKN. DENNIS3 Camphorlaurel Court, Stretton, Brisbane, Queensland, 4116, AustraliaE. GRASCNRS, LSPCMIB Universite Paul Sabatier, 31062 Toulouse Cedex 9, FranceA. C. KNIPEFaculty of Life and Health Sciences, University of Ulster, Coleraine, Northern IrelandP. KVSKYDepartment 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, CanadaR.N. MEHROTRADepartment of Chemistry, JNV University, Jodhpur, IndiaK.C. WESTAWAYDepartment of Chemistry and Biochemistry, Laurentian University, Sudbury, Ontario P3E 2C6, Canada

Preface

The present volume, the forty-third in the series, surveys research on organic reaction mechanisms described in the available literature dated 2007. 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, 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 following unfortunate slippage in dates of publication of recent volumes it is hoped that the next will be published within nine months. This is a consequence of steps already taken to reduce progressively the delay between title year and publication date and thereby eventually regain our optimum production schedule.

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.