Organoselenium Chemistry I - Krief, Alain; Hevesi, Laszlo
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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 selenium based reagents and reactions have been discovered, which are able to perform specific transformations selectively and often under very mild conditions. The aim of this volume is to present the different selenium containing reagents now available to chemists, to mention the scope as well as the…mehr

Produktbeschreibung
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 selenium based reagents and reactions have been discovered, which are able to perform specific transformations selectively and often under very mild conditions. The aim of this volume is to present the different selenium containing reagents now available to chemists, to mention the scope as well as the limitations of their reactions, and to compare those which possess similar reactivities. The authors present the reagents in the order of increasing oxidation level around the selenium atom.
  • Produktdetails
  • Verlag: Springer, Berlin
  • Softcover reprint of the original 1st ed. 1988
  • Seitenzahl: 236
  • Erscheinungstermin: 6. Dezember 2011
  • Englisch
  • Abmessung: 244mm x 170mm x 12mm
  • Gewicht: 414g
  • ISBN-13: 9783642732430
  • ISBN-10: 3642732437
  • Artikelnr.: 36120694
Inhaltsangabe
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.- 2.1.1 N-dealkylation of Quaternary Ammonium Salts.- 2.1.2 N-dealkylation of Amines.- 2.1.3 Dealkylation of Alkyl Aryl Ethers,-Sulfides and-Selenides.- 2.1.4 Synthesis of Carboxylic Acids From Esters.- 2.2 Reduction Reactions Involving Hydrogen Selenide, Selenols, Selenocyanates, Triphenylphosphine Selenide and Related Compounds.- 2.2.1 Reduction of Benzyl Halides to Aryl Alkanes and of Iodo- and of Selenoketones to Ketones.- 2.2.2 Reduction of vic-Diheterosubstituted Alkanes to Alkenes.- 2.2.2.1 Selenolate Mediated Reduction of vic-Dihalogenoalkanes and Bromohydrins to Olefins.- 2.2.2.2 Reduction of Epoxides and Thiiranes to Olefins.- 2.2.3 Reduction of Disulfides to Thiolates.- 2.2.4 Reduction of Sulfoxides, Selenoxides and Telluroxides to Sulfides, Selenides and Tellurides Respectively.- 2.2.5 Reduction of Nitro-, Nitroso-, Hydroxylamino-, Azo-, Hydrazo-aromatic Compounds to Aromatic Amines and Reduction of Aryldiazonium Salts to Hydrazinium Salts.- 2.2.6 Reduction of Schiff's Bases to Amines: Application to the one Pot Reductive Amination of the Carbonyl Group.- 2.2.7 Reduction of Aldehydes and Ketones to Alcohols.- 2.2.8 Reduction of the Carbon-Carbon Double Bond of Enones.- 2.2.9 Reduction of Benzyl Selenides to Aryl Alkanes and of Methylselenoacetals Derived From Aromatic Carbonyl Compounds to Benzyl Methyl Selenides.- 2.3 Use of Copper (I) Benzeneselenolate.- 2.3.1 As the Precursor of Mixed Alkyl Phenylselenocuprates.- 2.3.2 As a Catalyst in the Synthesis of ?-Selenoketones from Selenolesters and Diazomethane.- 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.- 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.- 3.4.1 Synthesis of Acylic Derivatives of Carbonic Acid.- 3.4.2 Synthesis of Heterocycles Derived from Carbonic Acid.- 3.4.3 Synthesis of Carbonohydrazides, Semicarbazides, Carbazates and Carbonates.- 3.4.4 Oxidation of Formates and Formamides to Carbonates and Carbamates.- 3.4.5 Synthesis of Hydrogen Selenide and Some of its Application.- 3.4.6 Oxidation of Hydrazine to Diimide: Application to the Cis Hydrogénation of Olefins.- 3.4.7 Carbonylation of Alkyl Aryl Ketones to 1,3-Dicarbonyl Compounds: Application to the Synthesis of 4-Hydroxycoumarins.- 4. Reactions Involving Selenoxides and Related Derivatives.- 4.1 Reactions Involving Selenoxides.- 4.1.1 Oxidation of Sulfides, Amines and Acyl Hydrazines to Sulfoxides, Aminoxides, and to Symmetrical Diacyl Hydrazines, Respectively.- 4.1.2 Oxidation of Enediols to Dicarbonyl Compounds.- 4.1.3 Oxidative Conversion of Thiocarbonyl Compounds to Carbonyl Compounds.- 4.1.4 Oxidation of Trivalent Phosphorus Compounds to Their Oxides and of Thio- and Selenophosphorus Derivatives to Their Oxygenated Analogues.- 4.1.5 Oxidation of Olefins to vic-Glycols with Osmium Tetroxide-Selenoxide Reagent.- 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 Al