Organic Azides

• Most current state-of-the-art overview of this important class of compounds, encompassing many new and emerging applications
• The number of articles on organic azides continues to increase tremendously; on average, there are more than 1000 new publications a year
• Covers basic chemistry as well as state-of-the-art applications in life science and materials science
• World-ranked authors describe their own research in the wider context of azide chemistry
• Includes a chapter on safe synthesis and handling (azides can decompose explosively)

Forewords: Rolf Huisgen, Valery Fokin, and Barry Sharpless.

Preface.

List of Contributors.

Abbreviations.

PART 1: SYNTHESIS AND SAFETY.

1 Lab-Scale Synthesis of Azido Compounds: Safety Measures and Analysis (Thomas Keicher and Stefan Löbbecke).

2 Large-Scale Preparation and Usage of Azides (Jürgen Haase).

3 Synthesis of Azides (Teresa M.V.D. Pinho e Melo).

4 Azides by Olefin Hydroazidation Reactions (Jérôme Waser and Erick M. Carreira).

PART 2: REACTIONS.

5 The Chemistry of Vinyl, Allenyl, and Ethynyl Azides (Klaus Banert).

6 Small Rings by Azide Chemistry (Thomas L. Gilchrist and Maria José Alves).

7 Schmidt Rearrangement Reactions with Alkyl Azides (Scott Grecian and Jeffrey Aubé).

8 Radical Chemistry with Azides (Ciril Jimeno and Philippe Renaud).

9 Cycloaddition Reactions with Azides: An Overview (Christine Schilling, Nicole Jung and Stefan Bräse).

10 Dipolar Cycloaddition Reactions in Peptide Chemistry (Christian Wenzel Tornøe and Morten Meldal).

11 Photochemistry of Azides: The Azide/Nitrene Interface (Nina Gritsan and Matthew Platz).

12 Organoazides and Transition Metals (Werner R. Thiel).

PART 3: MATERIAL SCIENCES.

13 Azide-containing High Energy Materials (Thomas M. Klapötke and Burkhard Krumm).

14 Azide Chemistry in Rotaxane and Catenane Synthesis (Stéphanie Durot, Julien Frey, Jean-Pierre Sauvage and Christian Tock).

PART 4: APPLICATION IN BIOORGANIC CHEMISTRY.

15 Aza-Wittig Reaction in Natural Product Syntheses (Francisco Palacios, Concepción Alonso, Domitila Aparicio, Gloria Rubiales and Jesús M. de los Santos).

16 Azides in Carbohydrate Chemistry (Henning S.G. Beckmann and Valentin Wittmann).

Index.

"This book is timely and important - the first devoted entirely to azides to appear in 26 years. . . The editors are to be congratulated for attracting so many experts to produce an excellent work in a timely fashion that should find a place in all laboratories." (JACS, 2010)

Stefan Bräse was born in Kiel, Germany, in 1967 and studied chemistry in Göttingen, Bangor (UK) and Marseille (France). In 1995, he obtained his doctorate after working with Armin de Meijere at the University of Göttingen. After post-doctoral appointments at Uppsala University, Sweden (J.-E. Bäckvall) and The Scripps Research Institute, La Jolla, USA (K. C. Nicolaou), he began his independent research career at the RWTH Aachen associated with Dieter Enders in1997 and finished his habilitation in 2001. He became Professor at the University of Bonn that same year. Since 2003, he is Full Professor at the University of Karlsruhe - in October 2009 renamed to the Karlsruhe Institute of Technology. Stefan Bräse has published more than 100 publications and is recipient of the ORCHEM award in 2000. His research interests include methods in drug-discovery (including drug delivery), combinatorial chemistry towards the synthesis of biologically active compounds, total synthesis of natural products and nanotechnology.

Organic azides are energy-rich and flexible intermediates for organic synthesis. They have found a variety of uses as reagents for the synthesis of heterocycles, as a “masked” amino function in natural compound synthesis, as the most important precursors of nitrenes, and as detonators, blowing agents for polymers, and functional groups in pharmaceuticals. In the past decade completely new perspectives have been developed for the use of azides in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interfaces between chemistry, biology, medicine, and materials science.

Organic Azides: Syntheses & Applications is an essential guide to the use and applications of this important class of compounds. Topics covered include the following aspects:

• synthesis and safety of azides
• the chemistry of vinyl azides
• small rings by azide chemistry
• rearrangement reactions of azides
• radical chemistry with azides
• cycloaddition reactions with azides
• click chemistry with azides
• dipolar cycloaddition reactions in peptide chemistry
• photochemistry of azides, and the azide/nitrene interface
• organometallic chemistry with azides
• applications in materials science, including azides in high energy materials, polymers and combinatorial chemistry
• applications in bioorganic chemistry, including azides in carbohydrate chemistry, natural products synthesis and Staudinger ligation

Organic Azides: Syntheses & Application is a comprehensive, authoritative and up-to-date guide to these important reagents for organic chemists, drug discovery researchers, materials scientists and those interested in the chemistry of natural products.