Handbook of Fluorous Chemistry
J. A. Gladysz, D. P. Curran, I. T. Horvath
First Edition, 2004
Edited by the leading experts John Gladysz, Dennis Curran, and István Horváth, this handbook is the first to summarize all the essential aspects of this emerging field of chemistry. Whether the reader is seeking an introduction to the concept of fluorous biphase catalysis, summaries of partition coefficients involving fluorous and organic solvents, or information on the latest fluorous mixture separation techniques, this authoritative compilation of contributions, written by the world's top authors, provides key information needed for successfully working with the diverse and fascinating families of fluorous molecules. The large number of reliable experimental procedures in particular makes this the ideal guide for newcomers wanting to use this elegant method in the laboratory. In addition, experts will also find a wealth of important information concisely contained in one ready reference. The result is an indispensable resource for everyone currently working or intending to work in this field.
There are some differences in physical properties between perfluorinated and organic solvents, and they have only limited mutual miscibility. While this doesn't sound like an enormous distinction, it opens up myriad new possibilities. Specially developed fluorous phase reagents remain in the so-called fluorous phase, so that the product can be obtained from the organic phase in practically pure form. In recent years, this concept has undergone extensive further development. For example, the fluorous phase versions of protecting groups and reverse phase silica gel (FRP-silica) make work-ups much simpler. This concept is so ingenious that one is well advised to learn more of what this area has to offer.
The "Handbook of Fluorous Chemistry" provides the best opportunity to date for gaining familiarity with this topic. The book is comprehensive, covering everything from solvation and material properties (e.g. partition coefficients) to illustrated descriptions of typical protocols for fluorous phase chemistry, not to mention a few practical tips. Thus, several variations on the fluorous phase Mitsunobu reaction are described. For example, the use of FDEAD and FTTP permit simple separation of the side-products. In another example, a fluorous phase benzoic acid can be introduced for the inversion of alcohol stereochemistry; in this case, the product can be isolated rapidly, and the acid can be recovered after the subsequent hydrolysis. The general discussion of a broad spectrum of different methods is supplemented with concrete experimental procedures, so that a fluorous phase protocol is described for a great many synthetic problems.
The general commentary helps chemists to develop their own ideas, and
the comprehensive literature citations and recommendations enable the
reader to reproduce specific syntheses easily. For these reasons, this
book is recommended to all practicing chemists who are interested in
streamlining product work-up and downstream processing.
Fluorous Chemistry: Scope and Definition
A Personal View of the History of Fluorous Chemistry
Fluorous Solvents and Related Media
Strategies for the Recovery of Fluorous Catalysts and Reagents: Design and Evaluation
Ponytails: Structural and Electronic Considerations
Partition Coefficients Involving Fluorous Solvents
Separations with Fluorous Silica Gel and Related Media
Light Fluorous Chemistry - A User´s Guide
Getting Started in Synthesis: A Tabular Guide to Selected Monofunctional Fluorous Compounds
Highlights of Applications in Synthesis and Catalysis
Applications of Fluorous Compounds in Materials Chemistry
Fluorous Materials for Biomedical Uses
Fun and Games with Fluorous Chemistry