Oxidation of Alcohols to Aldehydes and Ketones
Gabriel Tojo, Marcos Fernández
First Edition, 2006
Springer, New York
The aim of this book is to help people performing routine operations in Organic Synthesis in a laboratory. This book, the first one in a series, focuses on the oxidation of alcohols to aldehydes and ketones. Probably, this is the most important routine operation in Organic Synthesis.
The oxidation of alcohols to aldehydes and ketones is one of the predominant reactions in organic chemistry, since aldehydes and ketones serve as starting material for a multitude of other reactions, but these compounds do not have the same broad commercial availability or stability of alcohols. The synthesis of aldehydes entails a selectivity problem - namely, their further oxidation to carboxylic acids - which can only be overcome through the selection of an appropriate oxidant.
The book “Oxidation of Alcohols to Aldehydes and Ketones” is dedicated to practical, working chemists. It contains reactions that work well, and covers reagents that are known as well as some novel ones. Since the descriptions of reagents include the range of possible reactions, side-reactions and compatibility with other functional groups and protecting groups, it is easy to understand why the treatment of some of the newer oxidants ended up being rather cursory. The list of reagents covers the range of available options quite well, and most synthetic problems will yield to an answer found in this book.
For the specific groups such as hypervalent iodine compounds, this monograph follows their historical development, and discusses reaction mechanisms, sets of reaction conditions and modifications, which further extend the range of possible transformations and at the same time facilitate improvements in the reaction selectivity. Special emphasis is placed on concrete synthesis procedures, which are often detailed enough as to make consultation of the primary literature unnecessary.
The authors’ approach has been to write a book that provides many practical tips, and that offers such an extensive collection of specific procedures that the work would more likely be kept in the laboratory rather than the library. In this aim, Tojo and Fernandez have most certainly succeeded. It’s hard to answer the question of whether a single copy in the library will be sufficient, given the importance of the reactions described, and it will be up to the discretion of individual research group leaders whether to invest in a lab copy. In any case, well-written books such as this one with pithy technical content and numerous specific procedures are always welcome in laboratories that have a strong synthesis orientation. However, libraries should still consider obtaining a reference copy, especially in the context of the other books of this series that have yet to appear.
1. Chromium-Based Reagents
2. Activated Dimethyl Sulfoxide
3. Hypervalent Iodine Compounds
4. Ruthenium-Based Oxidations
5. Oxidations Mediated by TEMPO and Related Stable Nitroxide
6. Oxidations by Hydride Transfer from a Metallic Alkoxide
7. Fe´tizon’s Reagent: Silver Carbonate on Celite
8. Selective Oxidations of Allylic and Benzylic Alcohols in the
Presence of Saturated Alcohols
9. Selective Oxidations of Primary Alcohols in the Presence of
10. Selective Oxidations of Secondary Alcohols in Presence of