Ketenes is a comprehensive, self-contained guide to all aspects of ketene chemistry.

Features:

• Includes all advances made from 1995 to the present, including updates from the literature and over 1,000 new references
• Includes sections on cycloaddition reactions, ketenes from esters, ketene reactions using polymer supports, and oxoquinone methides

Contents

Structure, Bonding, and Thermochemistry of Ketenes

• heoretical Studies of Ketenes.
• Molecular and Electronic Structure and Energy.
• Theoretical Studies of Ketene Reactions.
• Substituent Effects on Ketenes.
• Molecular Structure Determinations.
• Thermochemistry of Ketenes

Spectroscopy and Physical Properties of Ketenes

• Nuclear Magnetic Resonance Spectroscopy.
• Ultraviolet and Photoelectron Spectroscopy.
• Infrared Spectra.
• Dipole Moments.
• Mass Spectrometry and Gas Phase Ion Chemistry

Preparation of Ketenes

• Ketenes from Carboxylic Acids and Their Derivatives.
• Ketenes from Carboxylic Anhydrides.
• Ketenes from Acyl Halides and Activated Acids.
• Ketenes from Esters.
• Ketenes from Ester Enolates.
• Ketenes by Ester Pyrolysis.
• Other Preparations of Ketenes from Esters.
• Ketenes by Dehalogenation of ?-Halo Carboxylic Derivatives.
• Ketenes from Diazo Ketones (Wolff Rearrangements).
• Thermal Wolff Rearrangement.
• Photochemical Wolff Rearrangement.
• Ketenes by Photochemical and Thermolytic Methods.
• Ketenes from Cyclobutanones and Cyclobutenones.
• Ketenes from Photolysis of Cycloalkanones and Enones.
• Ketenes from Cytclohexadienones and Other Cycloalkenones.
• Ketenes from Dioxinones.
• Ketenes by Thermolysis of Alkynyl Ethers.
• Ketenes from Other Thermolytic and Photochemical Routes.
• Ketenes from Alkenylcarbene Metal Complexes.
• Ketene Formation under Acidic Conditions.
• Ketenes from Oxidation of Alkynes.
• Other Routes to Ketenes

Types of Ketenes

• Carbon-Substituted Ketenes.
• Alkylketenes.
• Alkenylketenes.
• Alkynylketenes and Cyanoketenes.
• Arylketenes.
• Cyclopropylketenes.
• Acylketenes.
• Imidoylketenes.
• Cumulene-Substituted Ketenes.
• Ketenes with Charged, Radical, or Carbenic Side Chains.
• Fulvenones.
• Triafulvenones.
• Pentafulvenones.
• Heptafulvenones.
• Oxoquinone Methides and Related Species.
• Nitrogen-Substituted Ketenes.
• Oxygen-Substituted Ketenes.
• Halogen-Substituted Ketenes.
• Fluoroketenes, Perfluoroalkylketenes and Perfluoroarylketenes.
• Chlorine, Bromine, and Iodine-Substituted Ketenes.
• Silyl-, Germyl-, and Stannylketenes.
• Phosphorous- and Arsenic-Substituted Ketenes.
• Sulfur-Substituted Ketenes.
• Metal-Substituted Ketenes.
• Lithium Ketenes (Lithium Ynolates) and Ynols.
• Boron-Substituted Ketenes.
• Other Metal-Substituted Ketenes and Metal Ketenides.
• Metal-Complexed Ketenes.
• Bisketenes.
• Ketenyl Radicals, Anions, and Cations.
• Cumulenones

Reactions of Ketenes

• Oxidation and Reduction of Ketenes (Electron Transfer).
• Photochemical Reactions.
• Thermolysis Reactions.
• Cycloaddition Reactions of Ketenes.
• Intermolecular [2+2] Cycloaddition.
• Dimerization of Ketenes.
• Cycloaddition with Alkenes and Dienes.
• Mechanism of Ketene [2+2].
• Cycloaddition of Ketenes with Nucleophilic Alkenes.
• Cycloaddition of Ketenes with Allenes.
• Cycloaddition of Ketenes with Alkynes.
• Cycloaddition of Ketenes with Imines.
• Cycloadditions of Ketenes with Other Substrates.
• Cycloaddition Reactions of Ketenes.
• Cycloadditions of Ketenes.
• Intramolecular Cycloadditions of Ketenes.
• Intermolecular and Intramolecular Cycloaddition of Ketenes with Carbonyl Groups.
• Nucleophilic Addition to Ketenes.
• Mechanisms.
• Theoretical Studies.
• Kinetics of Hydration: Neutral and Base Reactions.
• Acid-Catalyzed Hydration.
• Alcoholysis and Aminolysis.
• Nucleophilic Additions to Ketenes: Preparative Aspects.
• Hydride Addition.
• Oxygen Nucleophiles.
• Nitrogen Nucleophiles.
• Carbon Nucleophiles.
• Other Nucleophiles.
• Wittig Reactions.
• Electrophilic Addition to Ketenes.
• Protonation of Ketenes.
• Electrophilic Addition of Hydrogen Halides to Ketenes.
• Electrophilic Additions to Other Reagents.
• Oxygenation of Ketenes.
• Radical Reactions of Ketenes.
• Polymerization of Ketenes.
• Stereoselectivity in Ketene Reactions.
• Other Additions to Ketenes.
• Reaction with Diazomethanes.
• Reaction with Sulfur Dioxide.
• Ketene Reactions Using Polymer Supports

Index

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