Carboxylic Ortho Acid Derivatives: Preparation and Synthetic Applications

Preface

Chapter 1. Synthesis and Properties of Carboxylic Ortho Esters and Related Compounds

I. Introduction

II. Synthesis of Ortho Esters from Nitriles and Imidic Esters

III. Synthesis of Ortho Esters from Trihalomethyl Compounds and ?-Halo Ethers

IV. Synthesis of Ortho Esters from Other Ortho Esters

V. Formation of Ortho Esters by Reactions involving addition of Alcohols to Carbon-Carbon Multiple Bonds

VI. Synthesis of Ortho Esters from Carbonium Salts

VII. Synthesis of Cyclic and Spirocyclic Ortho Esters from Epoxides and Formate Esters or Lactones

VIII. Formation of Ortho Esters by Cyclizations of Acyloxy Compounds

IX. Synthesis of Carboxylic Ortho Esters from Tetraalkyl Orthocarbonates

X. Formation of Carboxylic Ortho Esters by Reactions of Dialkoxycarbenes with Alcohols

XI. Synthesis of Ortho Esters by Addition of Ketene Acetals to ?,?-Unsaturated Carbonyl Compounds

XII. Miscellaneous Reactions Which Yield Ortho Esters

XIII. Synthesis of Peroxy and Hydroperoxy Ortho Esters

XIV. Synthesis of Acyloxy Ortho Esters

XV. Physical Properties of Ortho Esters

References

Chapter 2. Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

I. Hydrolysis of Carboxylic Ortho Esters

II. Reactions of Carboxylic Ortho Esters Which Yield Ethers

III. Reactions of Carboxylic Ortho Esters Which Yield Carboxylate Esters

IV. Conversion of Carbonyl Compounds to Hemiacetals, Acetals, and Ketals

V. Reactions of Carboxylic Ortho Esters Which Yield Esters of Acids Other than Carboxylic and Carbonic Acids

VI. Reactions of Carboxylic Ortho Esters Which Yield Alkyl Halides

References

Chapter 3. Reactions of Ortho Esters Which Result in Carbon-Nitrogen or Carbon-Phosphorus Bond Formation

I. Introduction

II. Reactions Which Yield Acyclic Products

III. Reactions Which Yield Nitrogen Heterocycles

IV. Reactions Resulting in Carbon-Phosphorus Bond Formation

References

Chapter 4. Reactions of Ortho Esters Which Involve Carbon-Carbon or Carbon-Hydrogen Bond Formation

I. Introduction

II. Reactions of Ortho Esters with Organometallic Compounds

III. Reactions of Ortho Esters with Metal Hydrides

IV. Reactions of Ortho Esters with Compounds Which have Activated Carbon-Hydrogen Bonds

V. Electrophilic Additions of Orthocarboxylates to Carbon-Carbon Double Bonds

VI. Aromatic Substitution Reactions of Ortho Esters

VII. Reactions of Ortho Esters with Ethyl Diazoacetate and with Diazo Ketones

VIII. Miscellaneous Ortho Ester Addition Reactions Which Form Carbon-Carbon Bonds

IX. Elimination Reactions of Ortho Esters-Synthesis of Ketene Acetals

X. Other Elimination Reactions of Ortho Esters

References

Chapter 5. Carbohydrate Ortho Esters

I. Introduction

II. Synthesis and Properties of Carbohydrate Ortho Esters

III. Reactions of Carbohydrate Ortho Esters Which Yield Non-Ortho Ester Products

References

Chapter 6. Thioorthocarboxylates, Thioorthocarbonates, and Related Compounds

I. Introduction

II. Syntheses of Trithioorthocarboxylates, Tetra-Thioorthocarbonates, and Related Compounds

III. Properties and Sources of Thioorthocarboxylic and Thioorthocarbonic Acid Derivatives

IV. Reactions of Thioorthocarboxylates, Thioortho-Carbonates, and Related Compounds

References

Chapter 7. Amide Acetals, Ester Aminals, and Ortho Amides

I. Introduction

II. Syntheses of Amide Acetals, Ester Aminals, and Ortho Amides

III. Properties and Sources of Amide Acetals, Ester Aminals, and Ortho Amides

IV. Reactions of Amide Acetals, Ester Aminals, and Ortho Amides

References

Author Index

Subject Index