Tin in Organic Synthesis

1st Edition - February 10, 1987
Authors: Michel Pereyre, Jean-Paul Quintard, Alain Rahm
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 1 - 6 1 0 7 - 5

Tin in Organic Synthesis is a systematic presentation of the organic chemistry of tin. This book discusses the significant advances that have been made with regard to the… Read more

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Tin in Organic Synthesis is a systematic presentation of the organic chemistry of tin. This book discusses the significant advances that have been made with regard to the applications of organotin compounds as reagents or intermediates in organic synthesis and points out directions for future developments. This monograph is comprised of 17 chapters divided into four sections. Following a brief introduction to organotin chemistry, the production of the organotin reagents, which are most usually employed in organic synthesis, is described. Special emphasis is placed on the creation of a fresh tin-carbon bond, a preliminary step in numerous fruitful applications. The following chapters are devoted to synthetic applications involving tin-hydrogen, tin-carbon, and tin-heteroatom bonds. The reduction of organic halides, carbonyl compounds, thio, nitrogen compounds, unsaturated carbon-carbon bonds, and seleno and telluro compounds is considered. The discussion then turns to electrophilic cleavages of tin-carbon bonds, which are of possible interest in organic synthesis, along with transmetallation and metallation of organotin compounds. The creation of new carbon-carbon bonds through substitution, addition, or elimination reactions is also examined. The remaining chapters focus on organotin alkoxides, organotin enolates, organotin oxides and peroxides, and organotin esters. This book will be of interest to students and researchers in the field of organic chemistry.

Part One: Introduction to Organotin Chemistry 1 General Organotin Chemistry 1.1 Nomenclature 1.2 Literature 1.3 Tin and its Bonds 1.4 Some Physical Data 1.5 Toxicity and Hazards 2 Preparation of Organotin Reagents 2.1 Synthesis of Basic Organotin Reagents 2.2 Creation of a Fresh Tin-Carbon Bond 2.3 Functional Transformations of Groups Bound to Tin ReferencesPart Two: Synthetic Applications Involving Tin-Hydrogen Bonds 3 Reduction of Organic Halides 3.1 General 3.2 Reduction of Simple Organic Halides and Polyhalides 3.3 Chemoselective Reduction of Polyfunctional Halides 3.4 Stereochemistry 3.5 Reductions with Free-Radical Rearrangement or Fragmentation 4 Reduction of Carbonyl Compounds 4.1 Aldehydes and Ketones 4.2 Acyl Halides 4.3 Esters and Related Compounds 5 Reduction of Thio, Seleno and Telluro Compounds 5.1 Thio Derivatives 5.2 Seleno Derivatives 5.3 Telluro Derivatives 6 Reduction of Nitrogen Compounds 6.1 Isocyanides, Isocyanates and Related Compounds 6.2 Nitro Compounds 6.3 Miscellaneous Reactions 7 Reduction of Unsaturated Carbon-Carbon Bonds 7.1 αβ-Unsaturated Ketones and Aldehydes 7.2 αβ-Unsaturated Nitriles and Esters 7.3 Functionalization via Mercuric Compounds ReferencesPart Three: Synthetic Applications Involving Tin-Carbon Bonds 8 Access to Carbon-Hydrogen and Carbon-Heteroatom Bonds 8.1 Carbon-Hydrogen Bonds 8.2 Carbon-Halogen Bonds 8.3 Carbon-Oxygen Bonds; Related Oxidation Reactions 8.4 Other Carbon-Heteroatom Bonds 9 Transmetallation and Metallation of Organotin Compounds 9.1 General Features of Transmetallation and Metallation Reactions 9.2 Transmetallation of Vinyl Organotin Compounds 9.3 Transmetallation of α-Heterosubstituted Organotin Compounds 9.4 Transmetallation of Benzyl- and Allyl-Tin Compounds 9.5 Transmetallation of Miscellaneous Organotin Compounds 9.6 Metallation of Organotin Compounds 10 Access to Carbon-Carbon Bonds 10.1 Via Substitution Reactions 10.2 Via Addition Reactions 10.3 Via Elimination Reactions ReferencesPart Four: Synthetic Applications Involving Tin-Heteroatom Bonds 11 Organotin Alkoxides 11.1 In Substitution Reactions 11.2 In Oxidation Reactions 11.3 In Addition Reactions 11.4 As Catalysts 12 Organotin Enolates 12.1 Organotin(IV) Enolates 12.2 Tin(II) Enolates 13 Organotin Oxides and Peroxides 13.1 Oxides 13.2 Peroxides 14 Organotin Esters 14.1 Carboxylates 14.2 Other Esters 15 Organotin Compounds with Tin-Nitrogen Bonds 15.1 Simple Amines 15.2 Other Compounds with Sn-N Bonds 16 Organotin Compounds with Tin-Sulphur Bonds 16.1 Synthesis of Sulphides 16.2 Synthesis of Thiol Esters 16.3 Synthesis of Acylsulphenyl Chlorides 16.4 Conversion of Carbonyl to Thiocarbonyl Units 17 Organotin Compounds with Tin Bonds to Miscellaneous Elements 17.1 Tin-Tin Bonds 17.2 Tin-Metal Bonds 17.3 Tin-Halogen BondsReferencesIndex