Modern Phosphonate Chemistry is a unique, up-to-date reference that summarizes the role of phosphonates in traditional and modern organic synthesis

Features:

• Covers the main classes of functionalized phosphonates involved in modern synthetic chemistry
• Gives examples of fundamental early studies and comprehensive coverage of modern aspects of the field
• Presents synthesis methods, chemistry, properties, and applications in organic synthesis as a function of the nature of the groups present in the side chain
• Emphasizes carbanionic procedures, arguably now the best approach to elaborated phosphonates
• Includes 600 reaction schemes and 4600 refere

Contents

1-Alkynylphosphonates

• Synthesis of 1-Alkynylphosphonates
• Synthetic Applications of 1-Alkynylphosphonates
• Reduction of the Triple Bond
• Hydration of the Triple Bond
• Cycloaddition Reactions
• Reactions Involving Zirconacycles
• Addition Reactions of the Triple Bond
• Isomerization of Alkynylphosphonates
• Reactions of 3-Halogenopropynylphosphonates
• Reactions of the Phosphonyl Group

Silylphosphonates

• Synthesis of Silylphosphonates
• Dialkyl 1-Silylalkylphosphonates
• Dialkyl 2-Silylalkylphosphonates
• Dialkyl 3- and 4-Silylalkylphosphonates
• Synthetic Applications of Silylphosphonates
• Dialkyl 1-(Trimethylsilyl)methylphosphonates
• Diethyl 2-(Trimethylsilyl)-1-(ethoxycarbonyl)ethylphosphonate
• Dimethyl 2-(tert-Butyldimethylsilyl)-2-oxoethylphosphonate
• Diethyl 2-Cyano-2-(trimethylsilyl)ethylphosphonate

A-Halogenophosphonates

• Synthesis of a-Halogenophosphonates
• a-Monohalogenophosphonates
• a,a-Dihalogenophosphonates
• a,a,a-Trihalogenophosphonates
• Reactions of a-Halogenophosphonates
• a-Monohalogenophosphonates
• a,a-Dihalogenophosphonates
• a,a,a-Trihalogenophosphonates
• Reactions of the Phosphonyl Group

Epoxyphosphonates

• Synthesis of Epoxyphosphonates
• Dialkyl 1,2-Epoxyalkylphosphonates
• Dialkyl 2,3-Epoxyalkylphosphonates
• Dialkyl 3,4-Epoxyalkylphosphonates
• Dialkyl 4,5-, 5,6-, 6,7-, 7,8-, and 8,9-Epoxyalkylphosphonates
• Synthesis of Fosfomycin
• Synthetic Applications of Epoxyphosphonates
• 1,2-Epoxyalkylphosphonates
• 2,3-Epoxyalkylphosphonates
• 3,4-Epoxyalkylphosphonates

Formylphosphonates

• Synthesis of Formylphosphonates
• Dialkyl Formylphosphonates
• Dialkyl 1-Formylalkylphosphonates
• Dialkyl 2-Formylalkylphosphonates
• Dialkyl 3-Formylalkylphosphonates
• Dialkyl 4-Formylalkylphosphonates
• Dialkyl w-Formylalkylphosphonates
• Synthetic Applications of Formylphosphonates
• Reactions of the Carbonyl Group
• Reactions of the Methylene Group
• Heterocyclic Systems with Phosphonylated Substituents
• Horner-Wadsworth-Emmons Reactions
• Phosphonoacetaldehyde in Nature
• Reductive Amination
• Aminocarboxylation (Strecker and Related Reactions) Reactions of the Phosphonyl Group: Dealkylation

Cyanophosphonates

• Synthesis of Cyanophosphonates
• Dialkyl Cyanophosphonates
• Dialkyl 1-Cyanoalkylphosphonates
• Dialkyl 2-Cyanoalkylphosphonates
• Dialkyl 3-, 4-, 5-, and 6-Cyanoalkylphosphonates
• Synthetic Applications of Cyanophosphonates
• Reactions of Diethyl Cyanophosphonate.
• Horner-Wadsworth-Emmons Reactions of Dialkyl Cyanomethylphosphonates: Preparation of a,b-Unsaturated Nitriles
• Horner-Wadsworth-Emmons Reactions of Phosphonocrotononitriles: Preparation of a,b,g,d-Unsaturated Nitriles
• Elaboration of Horner-Wadsworth-Emmons-Produced a,b-Unsaturated Nitriles
• Cycloaddition Reactions
• Reactions of the Cyano Group
• Reactions of the Phosphonyl Group: Dealkylation

Ketophosphonates

• Synthesis of Ketophosphonates
• Dialkyl 1-Oxoalkylphosphonates
• Dialkyl 2-Oxoalkylphosphonates
• Dialkyl 3-Oxoalkylphosphonates
• Dialkyl w-Oxoalkylphosphonates
• Synthetic Applications of Ketophosphonates
• Reactions of Dialkyl w-Oxoalkylphosphonates with Conservation of the P-C Bond
• Reactions of Dialkyl w-Oxoalkylphosphonates with Cleavage of the P-C Bond
• Reactions of Dialkyl 2-Oxoalkylphosphonates
• Reactions of the Phosphonyl Group

Carboxyphosphonates

• Synthesis of Carboxyphosphonates
• Dialkyl (Alkoxycarbonyl)phosphonates
• Dialkyl 1-(Alkoxycarbonyl)alkylphosphonates
• Diethyl 1-(Hydroxycarbonyl)methylphosphonate
• Dimethyl 1-(Methoxycarbonyl)vinylphosphonate and
• Diethyl 1-(Ethoxycarbonyl)vinylphosphonate
• Dialkyl 1-(Alkoxycarbonyl)-1-diazomethylphosphonates
• Dialkyl 2-(Alkoxycarbonyl)alkylphosphonates
• Dialkyl 3-,4-,5- and 6-(Alkoxycarbonyl)alkylphosphonates Dialkyl 1-Oxo-w-(alkoxycarbonyl)alkylphosphonates
• Dialkyl 2-Oxo-w-(alkoxycarbonyl)alkylphosphonates
• w-Amino-w-(hydroxycarbonyl)alkylphosphonic Acids
• Synthetic Applications of Carboxyphosphonates
• Reactions of the Alkoxycarbonyl Group: Preparation of w-Aminoalkylphosphonic Acids
• Horner-Wadsworth-Emmons Reactions of Dialkyl 1-(Alkoxycarbonyl)methylphosphonates: Preparation of a,b-Unsaturated Esters
• Horner-Wadsworth-Emmons Reactions of Phosphonocrotonates: Preparation of a,b-g,d-Unsaturated Esters
• Elaboration of Horner-Wadsworth-Emmons -Produced a,b-Unsaturated Esters
• Reactions of the Phosphonyl Group

Abbreviations
Syntheses of Compounds Useful in Phosphonate Chemistry
Important Literature Resources in Phosphonate Chemistry
PKa Values of Diethyl Phosphonates
Index

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