Organic Azides. Syntheses and Applications

  • ID: 2175000
  • Book
  • 536 Pages
  • John Wiley and Sons Ltd
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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.
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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.

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"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)

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