Organoborane Chemistry

1st Edition - January 1, 1975
Author: Thomas Onak
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 5 3 6 1 - 4

Organoborane Chemistry deals with the chemistry of organoboranes, with emphasis on compounds containing a carbon-boron bond. The structure and physical properties of organoboranes… Read more

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Organoborane Chemistry deals with the chemistry of organoboranes, with emphasis on compounds containing a carbon-boron bond. The structure and physical properties of organoboranes are discussed, along with the reactions of three-coordinate and four-coordinate organoboranes, organodiboranes, and other organopolyboranes such as organotetraboranes and organopentaborane compounds. Comprised of seven chapters, this book begins with an overview of multistep synthetic or degradative reactions involving organoboron compounds, along with the nomenclature for such compounds. The next chapter examines the structure and physical properties of organoboranes, with emphasis on boron-carbon bond lengths, electronic transitions, and molecular orbital calculations. Subsequent chapters focus on three-coordinate and four-coordinate organoboranes, together with their synthesis, reactions, and properties; hydroboration and dehydroboration of organodiboranes; and the synthesis, reactions, and physical properties of other organopolyboranes such as organotetraboranes, organopentaborane compounds, and organodecaborane compounds. The final chapter is devoted to cyclic boron-carbon systems and the applications of organoboron compounds. This monograph should be of interest to organic chemists.

PrefaceChapter 1 Introduction and Nomenclature TextChapter 2 Structure and Physical Properties of Organoboranes 2-1. Boron-Carbon Bond Lengths 2-2. Boron-Carbon Bonding Characteristics 2-3. Nuclear Magnetic Resonance Boron-11 Proton Spin Coupling 2-4. Vibrational Spectroscopy 2-5. Electronic Transitions 2-6. Mass Spectrometry 2-7. Molecular Orbital Calculations 2-8. Thermodynamic Properties 2-9. Miscellaneous PropertiesChapter 3 Three-Coordinate Organoboranes 3-1. Boron-Carbon Bond Construction Transmetallation Redistribution and Exchange Reactions Hydroboration Haloboration Modified Friedel-Crafts Reaction Cyclization by Loss of H2 Diboration with Diboron(4) Compounds Formation of Boron-Carbon Bonds by the Action of Metals (or Metal Boron Compounds) on Halides Miscellaneous Preparative Reactions 3-2. Boron-Carbon Bond Cleavage and Other Reactions Protodeboronation and Hydrolysis of the Carbon-Boron Bond Autoxidation Action of Peroxides and Related Compounds Halogens Reactions of Organoboranes with N-Chloroamines Other Oxidative Reactions Radical Reactions Transmetallation Dehydroboration and Isomerization Reactions Other Elimination Reactions Reactions with Unsaturated Systems Migration of Halogen from Carbon to Boron Migration of Boron-Attached Organic Group to an Electropositive Center: Organoboranes as Alkylating (or Arylating) Agents Hydrogenolysis Reactions of Organoboranes with Alkali Metals Miscellaneous ReactionsChapter 4 Four-Coordinate Organoboranes 4-1. Organoborohydride Ions Synthesis Reactions and Properties 4-2. Organoborane-Lewis Base Adducts, RBXYD (D = Donor Group) Synthesis and Stability Reactions 4-3. Organoboronium Ions 4-4. Carbon Monoxide-Borane; H3BCO Synthesis Reactions Physical PropertiesChapter 5 Organodiboranes 5-1. Synthesis Exchange Reactions Reductions with Metal Hydrides Hydroboration Reduction of Organoboron Esters and Halides with Diborane Dehydroboration Insertion Miscellaneous Preparative Reactions 5-2. Reactions Hydrolysis, Alcoholysis, and Related Reactions Oxidation and Oxidative Hydrolysis Disproportionation and Exchange Reactions Hydroboration Coordination Compounds with Lewis Bases Diborane-Borane Equilibrium Miscellaneous Reactions 5-3. Physical Properties Structure Nuclear Magnetic Resonance Vibrational Spectroscopy Mass SpectrometryChapter 6 Other Organopolyboranes 6-1. Carbon Monoxide-Triborane 6-2. Organotetraboranes Alkyltetraborane(10) Compounds Tetraborane(8)carbonyl 6-3. Organopentaborane(9) Compounds Synthesis Reactions Physical Properties 6-4. Organopentaborane(11) Compounds 6-5. Organohexaborane(10) Compounds 6-6. Organodecaborane(14) Compounds Synthesis Reactions and Properties 6-7. Organic Derivatives of Large Closed-Cage Boron HydridesChapter 7 Supplementary Chemistry 7-1. Cyclic Boron-Carbon Systems 7-2. Influence of th e Organic Group on the Properties of the Attached Boron-Containing Moiety 7-3. Influence of Boron Substitution on th e Properties of the Attached Organic Group 7-4. Analysis of Organoboron Compounds 7-5. Uses and Applications of Organoboron CompoundsSupplementary Sources of InformationBibliographyAuthor IndexSubject Index