Organic Azides (eBook, PDF)

Syntheses and Applications

• Format: PDF

Produktbeschreibung

* 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)

Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 536
• Erscheinungstermin: 23. September 2011
• Englisch
• ISBN-13: 9780470682524
• Artikelnr.: 37298733

Autorenporträt

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.

Inhaltsangabe

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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Foreword: Rolf Huisgen and Barry Sharpless Preface List of Contributors
Abbreviations PART 1: SYNTHESIS + SAFETY Chapter 1: Safety Issues about
Azide Compounds Thomas Keicher and Stefan Löbbecke 1.1 Introduction 1.2
Properties that impose restrictions on lab-scale handling of azides 1.3
Laboratory safety instructions for the small scale synthesis of azido
compounds 1.4 Analyzing safety-related properties of azides 1.5 References
Chapter 2: Large Scale Preparation of Azides Jürgen Haase 2.1 Introduction
2.2 Precursor azides, technical production and properties 2.3 Examples for
the use of azides on a technical scale 2.4 The future of commercial-scale
azide chemistry 2.5 References Chapter 3: Synthesis of Azides Teresa M. V.
D. Pinho e Melo 3.1 Introduction 3.2 Synthesis of Alkyl Azides 3.3
Synthesis of Aryl Azides 3.4 Synthesis of Acyl Azides 3.5 References
Chapter 4: Azides by Hydroazidination Reactions Jérôme Waser and Erick
Carreira 4.1 Introduction 4.2 Conjugate Addition of Hydrazoic Acid and Its
Derivatives 4.3 Addition of Hydrazoic Acid and its Derivatives to
Non-Activated Olefins 4.4 Cobalt-Catalyzed Hydroazidation 4.5 Conclusion
4.6 References PART 2: REACTIONS Chapter 5: The Chemistry of Vinyl,
Allenyl, and Ethynyl Azides Klaus Banert 5.1 Introduction and Early
Synthetic Methods for Vinyl Azides 5.2 Routes to Vinyl Azides Developed in
the Period 1965 - 1970 5.3 New Methods to Prepare Vinyl Azides 5.4
Reactions of Vinyl Azides 5.5 The Chemistry of Allenyl Azides 5.6
Generation of Ethynyl Azides 5.7 Conclusion 5.8 References Chapter 6: Small
Rings by Azide Chemistry Thomas Gilchrist and Maria Alves 6.1 Introduction
6.2 2H-Azirines 6.3 Aziridines 6.4 Triaziridines 6.5 Azetidinones 6.6
References Chapter 7: Schmidt Rearrangement Reactions with Alkyl Azides
Scott Grecian and Jeffrey Aubé 7.1 Introduction and Early Attempts
(1940-1960) 7.2 Schmidt reactions of alkyl azides with carbonyl compounds
7.3 Schmidt reactions of alkyl azides with carbocations 7.4 Metal-mediated
Schmidt reactions of alkyl azides with alkenes and alkynes 7.5 Reactions of
alkyl azides with a,b-unsaturated ketones 7.6 Reactions of alkyl azides
with epoxides 7.7 Combined Schmidt rearrangement cascade reactions 7.8
Schmidt rearrangements in the total synthesis of natural products 7.9
Schmidt rearrangements of alkyl azides in the synthesis of interesting
non-natural products 7.10 Schmidt rearrangements of hydroxyalkyl azides
toward biologically relevant compounds 7.11 Final Comments 7.12
Acknowledgments 7.13 References Chapter 8: Radical Chemistry with Azides
Ciril Jimeno and Philippe Renaud 8.1 Introduction 8.2 Addition of the
azidyl radical onto alkenes 8.3 Azidation of carbon centered radicals 8.4
Aminyl and amidyl radicals via reduction of azides 8.5 Fragmentation
reaction of alpha-azidoalkyl radicals 8.6 Conclusions Chapter 9:
Cycloaddition Reactions with Azides C. Schilling, N. Jung and Stefan Bräse
9.1 Huisgen 1,3-dipolar cycloaddition 9.2 Copper-Catalyzed Azide-Alkyne
Cycloaddition (CuAAC) 9.3 Acceleration of the Click Reaction 9.4
Copper-free Click chemistry 9.5 Ruthenium-Catalyzed Azide-Alkyne
Cycloaddition (RuAAC) 9.6 Use of other metals for the cycloaddition of
azides and alkynes: Ni(II), Pt(II), Pd(II) 9.7 Cycloaddition reactions with
azides for the synthesis of tetrazoles 9.8 Click chemistry for the
synthesis of dihydrotriazoles 9.9 Cycloaddition reactions with azides to
give thiatriazoles 9.10 References Chapter 10: Dipolar Cycloaddition
Reactions in Peptide Chemistry Christian Wenzel Tornøe and Morten Meldal
10.1 Introduction 10.2 Amino Acid Derivatives by DCR 10.3 Peptide Backbone
Modifications by DCR 10.4 Other Peptide Modifications by DCR 10.5
Macrocyclization by DCR 10.6 Dendrimers and Polymers 10.7 Isotopic Labeling
by DCR 10.8 Perspective 10.9 References Chapter 11: Photochemistry of
Azides: The Azide/Nitrene Interface Matthew Platz and Nina Gritsan 11.1
Introduction 11.2 Photochemistry of hydrazoic acid (HN3) 11.3
Photochemistry of alkyl azides 11.4 Photochemistry of vinyl azides 11.5
Photochemistry of carbonyl azides and azide esters 11.6 Photochemistry of
phenyl azide and its simple derivatives 11.7 Conclusion 11.8
Acknowledgements 11.9 References Chapter 12: Organoazides and Transition
Metals Werner Thiel 12.1 Introduction 12.2 Metal complexes co-crystallized
with an organoazide 12.3 Cationic metal complexes with organoazide
containing anions 12.4 Metal complexes with ligands bearing a
non-coordinating organoazide unit 12.5 Metal complexes with an intact,
coordinating and linear organoazide ligand 12.6 Metal complexes with an
intact, coordinating but bent organoazide ligand 12.7 Organoazides reacting
with other metal bound ligands 12.8 References PART 3: MATERIAL SCIENCES
Chapter 13: Azide-Containing High Energy Materials Thomas Klapötke and
Burkhard Krumm 13.1 Introduction 13.2 Organic Azides 13.3 Acknowledgments
13.4 References Chapter 14: Azide Chemistry for Molecular Machines
Stephanie Durot, Julien Fry, Jean-Pierre Sauvage and Christian Took 14.1
Introduction 14.2 Purely organic rotaxanes and catenanes 14.3 Transition
metal templated approaches 14.4 Conclusion 14.5 References PART 4:
APPLICATION IN BIOORGANIC CHEMISTRY Chapter 15: Aza-Wittig Reaction in
Natural Product Syntheses Francisco Palacios, Concepción Alonso, Domitila
Aparicio, Gloria Rubiales and Jesús M. de los Santo 15.1 Introduction 15.2
Intermolecular aza-Wittig reaction 15.3 Intramolecular aza-Wittig reaction
15.4 Conclusions 15.5 Acknowledgments 15.6 References Chapter 16: Azides in
Carbohydrate Chemistry Henning S. G. Beckmann and Valentin Wittmann 16.1
Introduction 16.2 Synthesis of Azide-Containing Carbohydrates 16.3 Azides
as Protecting Groups during Aminoglycoside Synthesis 16.4 Azides as
Non-Participating Neighboring Groups in Glycosylations 16.5 Glycosyl Azides
as Precursors for Glycosyl Amides 16.6 Synthesis of Glycoconjugates via
Azide-Alkyne [3+2] Cycloaddition 16.7 Metabolic Oligosaccharide Engineering
16.8 References Key Word Index

Rezensionen

"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)