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Chemistry Book from C.H.I.P.S.

Modern Phosphonate Chemistry
by Philippe Savignac

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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Modern Phosphonate Chemistry
by Philippe Savignac
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