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Silicon-mediated Transformations of Functional Groups



Silicon-mediated Transformations of Functional Groups

Helmut Vorbrueggen

ISBN: 978-3-527-60592-7 March 2006 378 Pages


In the first work to comprehensively cover this all-important topic, the recognized expert Helmut Vorbrüggen provides both organic and bioorganic chemists with much new and valuable information for preparative synthesis.
Although every organic chemist may be familiar with different aspects of silylation for the protection of functional groups, this book covers the concept of protection while simultaneously silylating-activating various functional groups, such as amides and ureas. This novel methodology opens thus numerous synthetic pathways
while effecting the elimination of water in it volatile persilylated form under rather mild reaction conditions, which are often advantageous compared to conventional methods.
The compact form and clear structure of this monograph make this a long-awaited ready reference.

From the contents:

* Techniques of Preparative Silylations-Desilylations
* Preparation and Properties of Siliconoxy-Leaving Groups
* Reactions of Free and Derivatized Carboxylic Acids and Carbon Dioxide
* Reactions of Aldehydes and Ketones
* Reactions of Alcohols, Ethers and Epoxides
* Reaction of N-O Systems
* Reactions of S-O and Se-O Systems
* Cyclizations and Ring Enlargements
* Base and Acid-Catalyzed as well as Thermal Eliminations of Trimethylsilanol. Peterson Reactions
* Formation of Carbon-Phosphorous Double- and Triple Bonds
* Reductions and Oxidations
* Dehydration-Activation as well as Silylation of Inorganic and Organic Salts and Metalorganic Compounds
* Formation of Polymers

1. Introduction.

2. Techniques of Preparative Silylation—Desilylations.

3. Preparation and Properties of Siliconoxy Leaving Groups.

4. Reactions of Free and Derivatized Carboxylic Acids and Carbon Dioxide.

5. Reactions of Aldehydes and Ketones.

6. Reactions of Alcohols, Ethers, Silyl Ethers, Epoxides, and Haloalkanes.

7. Reactions of N-O Systems.

8. Reactions of S-O and Se-O Systems.

9. Cyclizations and Ring Enlargements.

10. Base-catalyzed, Acid-catalyzed and Thermal Eliminations of Trimethylsilanol, Peterson Reactions.

11. Formation of Carbon—Phosphorous Double Bonds.

12. Reductions and Oxidations.

13. Dehydration–Halogenation–Activation and Silylation of Inorganic and Organic Salts and Metallorganic Compounds.

14. Formation of Organic and Inorganic Polymers.


Subject Index.

Author Index.

"…very informative and should be of great interest to practicing organic chemists." (Journal of the American Chemical Society, October 26, 2005)

“This handbook is a clear, compact compilation … an essential practical and reference book for the research chemist.”  (Applied Organometallic Chemistry, May 2005)