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Organoselenium Chemistry I Functional Group Transformations

During the last fifteen years organoselenium chemistry underwent a spectacular mutation: from an exotic area of science practised by a few specialists it became a relatively well mastered and widely used methodology of synthetic organic chemistry. The key to this success is that a fair number of sel...

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Bibliographic Details
Main Authors: Krief, Alain, Hevesi, Laszlo (Author)
Format: eBook
Language:English
Published: Berlin, Heidelberg Springer Berlin Heidelberg 1988, 1988
Edition:1st ed. 1988
Subjects:
Chemistry, Organic
Organic Chemistry
Online Access:
Collection: Springer Book Archives -2004 - Collection details see MPG.ReNa
Table of Contents:
  • 1. Introduction
  • 1.1 Historical Review
  • 1.2 Abundance and Distribution of Selenium
  • 1.3 Selenium in Plants
  • 1.4 Selenium Toxicity in Animals
  • 1.5 Enzymic Role of Selenium
  • 1.6 Ecological Aspects of Selenium in Human Health
  • 1.7 Extraction of Selenium
  • 1.8 Industrial Uses of Selenium
  • 1.9 Selenium: Structure, Physical and Chemical Properties
  • 2. Reactions Involving Hydrogen Selenide, Selenols and Related Compounds
  • 2.1 Reactions Involving the Nucleophilicity of Hydrogen Selenide, Selenols and Related Compounds
  • 2.2 Reduction Reactions Involving Hydrogen Selenide, Selenols, Selenocyanates, Triphenylphosphine Selenide and Related Compounds
  • 2.3 Use of Copper (I) Benzeneselenolate
  • 2.4 Reduction of Dienes to Olefins With Dichloro Bis (Diphenyl Selenide) Platinum (II)
  • 3. Reactions Involving Metallic or Amorphous Selenium with Organic Molecules
  • 3.1 Transformation of (Z) Alkenes to Their (E) Isomers
  • 8.2 Baeyer-Villiger Type Oxidation of Ketones to Esters and Lactones
  • 8.3 Oxidation of Selenides to Selenoxides and Selenones and of Sulfides to Sulfoxides or Sulfones
  • 9. Selenium Dioxide Oxidations
  • 9.1 Reactivity of SeO2 with Alkenes
  • 9.2 Reactivity of SeO2 Towards Acetylenic Hydrocarbons
  • 9.3 Reactivity of SeO2 with Carbonyl Compounds
  • 9.4 Oxidation of the Alkyl Chain of Aromatic and Heteroaromatic Compounds
  • 9.5 Oxidation of Benzylic and Allylic Alcohols
  • 9.6 Oxidation of Hydrazones, Imines, Oximes and Semicarbazones
  • 9.7 Conversion of Thio- and Selenocarbonyl Compounds to Carbonyl Compounds
  • 9.8 Reactions of Nitroalkanes: Synthesis of N-hydroxy Carboxamides and Nitriles
  • 9.9 Synthesis of Olefins from Phosphorus Ylides and Diazoalkanes
  • 9.10 Reaction ofSeO2 with Phosphines, Arsines, Stibines and Related Compounds
  • 9.11 Reaction with Hydrazines
  • 9.12 Reaction with Organometallics
  • 10. Reactions of Imidoselenium Compounds
  • 6.1 Oxidation of Phenols, Pyrocatechols and Hydroquinones
  • 6.2 Dehydrogenation of Ketones to Enones and Dienones
  • 6.3 Dehydrogenation of Lactones and Lactams to ?, ?-Unsaturated Compounds
  • 6.4 Oxidation of Alcohols to Carbonyl Compounds or to Enones and Dienones
  • 6.5 Oxidative Conversion of Thiols to Disulfides, Sulfides to Sulfoxides and of Phosphines to Phosphinoxides
  • 6.6 Oxidation of Amines
  • 6.7 Oxidation of Hydrazines
  • 6.8 Oxidation of Hydroxylamines
  • 6.9 Oxidation of the Alkyl Chain of Aromatic and Heteroaromatic Compounds
  • 6.10 Regeneration of Carbonyl Compounds
  • 6.11 Synthesis of ?-Selenocarbonyl Compounds from BSA and
  • 6.12 Synthesis of Allyl Alcohols from Allyl Silanes
  • 7. Reactions Involving Benzeneseleninyl Halides
  • 7.1 Oxidation of Aldoximes to Nitriles
  • 7.2 Oxidation of Amines
  • 7.3 Dehydrogenation of Carbonyl Compounds to Enones
  • 8. Reactions Involving Perseleninic Acids
  • 8.1 Oxidation of Olefins to Epoxides
  • 3.2 Oxidation of Cyclic and Poly cyclic Hydrocarbons and Heterocycles to Aromatic Compounds Using Elemental Selenium
  • 3.3 Oxido-reduction Reactions of Hydrocarbons
  • 3.4 Reactions Involving Carbon Monoxide and Catalytic Amounts of Selenium
  • 4. Reactions Involving Selenoxides and Related Derivatives
  • 4.1 Reactions Involving Selenoxides
  • 4.2 Oxidation of Alcohols to Carbonyl Compounds with Dimethylselenide/N-chlorosuccinimide
  • 4.3 Oxidative Conversion of sec-Benzylamines to Imines and Tertiary Benzylamines to Iminium Salts by Diphenylselenium Bis(trifluoroacetate)
  • 5. Reactions Involving Selenenyl Halides and Related Compounds
  • 5.1 Allylic Halogenation of Olefins
  • 5.2 Ring Expansion of 1,3-Dithiolans and 1,3-Dithians
  • 5.3 Oxidation of Alcohols to Carbonyl Compounds
  • 5.4 Synthesis of Oligonucleotides and Nucleoside Phosphoramidates
  • 6. Reactions Involving Benzeneseleninic Anhydride (BSA) and Related Reagents
  • 10.1 With Alkenes and Alkynes: Synthesis of Allylic and Propargylic Amines
  • 10.2 With Dienes: Synthesis of Cis Diaminoalkanes
  • 11. Reactions Involving Selenium Oxychloride and Selenium Tetrahalides
  • 11.1 Reactivity of Selenium Oxychloride
  • 11.2 Reactivity of Selenium Tetrafluoride
  • 11.3 Reactivity of Selenium Tetrachloride
  • References

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