Tin in Organic Synthesis

Tin in Organic Synthesis

1st Edition - February 10, 1987

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  • Authors: Michel Pereyre, Jean-Paul Quintard, Alain Rahm
  • eBook ISBN: 9781483161075

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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.

Table of Contents

  • 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


    Part 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


    Part 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


    Part 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 Bonds



Product details

  • No. of pages: 352
  • Language: English
  • Copyright: © Butterworth-Heinemann 1987
  • Published: February 10, 1987
  • Imprint: Butterworth-Heinemann
  • eBook ISBN: 9781483161075

About the Authors

Michel Pereyre

Jean-Paul Quintard

Alain Rahm

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