Silicon in Organic Synthesis - 1st Edition - ISBN: 9780408108317, 9781483142234

Silicon in Organic Synthesis

1st Edition

Butterworths Monographs in Chemistry and Chemical Engineering

Authors: Ernest W. Colvin
Editors: J E Baldwin A D Buckommgham S Danishefsky
eBook ISBN: 9781483142234
Imprint: Butterworth-Heinemann
Published Date: 1st January 1981
Page Count: 360
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Silicon in Organic Synthesis provides an introduction to the organic chemistry of silicon. This book places particular emphasis on the concept of silicon as a “ferryman,” mediating the transformation of one wholly organic molecule into another. The book begins by reviewing the discovery and development of organosilicon compounds. This is followed by separate chapters on the physical properties of organosilicon compounds; the preparation of α-metallated organosilanes, which play a key role in preparative organosilicon chemistry; migration/rearrangement reactions of silicon; the preparation and chemistry of vinylsilanes, allylsilanes, arylsilanes, and organosilyl metallic compounds. Subsequent chapters cover the synthesis of compounds such as alkene, alkynylsilanes, allenylsilanes, silylketenes, alkyl silyl ethers, acyloxysilanes, and silyl enol ethers. This book aims to serve as a timely introduction to organic chemistry for students and practitioners of synthetic organic chemistry, as well as provide a source of useful information and possibly of new ideas to those already experienced in the area.

Table of Contents

1 Introduction

2 Physical Properties of Organosilicon Compounds

2.1 Relative Bond Strengths

2.2 Electronegativity

2.3 p-Orbitals

2.4 P-Orbitals

3 The β-Effect

4 α-Metallated Organosilanes

4.1 Organometallic Addition to Vinylsilanes

4.2 Proton Abstraction

4.3 Metal-Halogen Exchange

4.4 Transmetallation

5 Rearrangement Reactions with Migration of Silicon

5.1 1,2-Rearrangements

5.2 1,3-Rearrangements

5.3 1,4-Rearrangements

5.4 1,5-Rearrangements

6 Organohalogenosilanes and Substitution at Silicon

7 Vinylsilanes

7.1 Preparation

7.2 Geometric Differentiation

7.3 Reactivity

7.4 Some other Reactions of Vinylsilanes

7.5 Addendum

8 αβ-Epoxysilanes as Precursors of Carbonyl Compounds and Heteroatom-Substituted Alkenes

8.1 Preparation

8.2 Isomerization

9 Allylsilanes

9.1 Preparation

9.2 Electrophilic Substitution

9.3 Other Selected Examples of Silyl Control of Carbonium Ion Formation and Collapse

9.4 Some Reactions not Involving Carbonium Ions

9.5 Addendum

10 Arylsilanes

10.1 Preparation

10.2 Electrophile-Induced Desilylation

11 Organosilyl Anions

11.1 Preparation

11.2 Reactions

12 Alkene Synthesis by 1,2-Elimination Reactions of β-Functional Organosilanes

12.1 β-Hydroxyalkylsilanes

12.2 β-Halogenoalkylsilanes and Related Species

12.3 Addendum

13 Alkynylsilanes and Allenylsilanes

13.1 Alkynylsilanes

13.2 Allenylsilanes

14 Silylketenes

15 Alkyl Silyl Ethers

15.1 Solvolysis

15.2 Trimethylsilyl Ethers

15.3 t-Butyldimethylsilyl Ethers

15.4 Addendum

16 Acyloxysilanes (Silyl Carboxylates)

17 Silyl Enol Ethers and Silyl Ketene Acetals

17.1 Preparation of Silyl enol Ethers

17.2 Preparation of Silyl Ketene Acetals

17.3 Reactions

17.3.1 Generation of Specific Enolate Anions

17.3.2 Lewis Acid-Catalysed Alkylation

17.3.3 Alkylation and α-Methylenation

17.3.4 Hydroxyalkylation and Related Reactions

17.3.5 Silyl Dienol Ethers and Bis(Silylenol) Ethers

17.3.6 Acylation

17.3.7 Hydroboration-Oxidation

17.3.8 Oxidation

17.3.9 Cycloaddition

17.3.10 Sigmatropic Rearrangements and Related Processes

17.3.11 Modified Acyloin Condensations and Related Reactions

17.3.12 1-Trimethylsilyl Trimethylsilyl Enol Ethers

17.3.13 Silyl Nitronates

17.4 Addendum

18 Trimethylsilyl-Based Reagents

18.1 Reagent Preparation

18.2 Ester and Ether Cleavage

18.3 Carbonyl Addition Processes

18.4 Other Addition Processes

18.5 Other Functionalized Silane Reagents

18.6 Addendum

19 Nitrogen-Substituted Silanes

19.1 Amino-Silanes

19.2 Oxidative Decyanation

19.3 Amides and Amide Bond Formation

20 Silicon-Substituted Bases and Ligands

21 Silanes as Reducing Agents

21.1 Hydrosilylation

21.2 Ionic Hydrogenation

21.3 Reductive Silylation

21.4 Deoxygenation Processes



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© Butterworth-Heinemann 1981
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About the Author

Ernest W. Colvin

About the Editor

J E Baldwin

A D Buckommgham

S Danishefsky

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