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Mechanochemical Organic Synthesis

1st Edition - April 23, 2016

Authors: Davor Margetic, Vjekoslav Štrukil

Hardback ISBN:

9 7 8 - 0 - 1 2 - 8 0 2 1 8 4 - 2

eBook ISBN:

9 7 8 - 0 - 1 2 - 8 0 2 5 2 5 - 3

Mechanochemical Organic Synthesis is a comprehensive reference that not only synthesizes the current literature but also offers practical protocols that industrial and academic… Read more

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Mechanochemical Organic Synthesis

is a comprehensive reference that not only synthesizes the current literature but also offers practical protocols that industrial and academic scientists can immediately put to use in their daily work. Increasing interest in green chemistry has led to the development of numerous environmentally-friendly methodologies for the synthesis of organic molecules of interest. Amongst the green methodologies drawing attention, mechanochemistry is emerging as a promising method to circumvent the use of toxic solvents and reagents as well as to increase energy efficiency.

The development of synthetic strategies that require less, or the minimal, amount of energy to carry out a specific reaction with optimum productivity is of vital importance for large-scale industrial production. Experimental procedures at room temperature are the mildest reaction conditions (essentially required for many temperature-sensitive organic substrates as a key step in multi-step sequence reactions) and are the core of mechanochemical organic synthesis. This green synthetic method is now emerging in a very progressive manner and until now, there is no book that reviews the recent developments in this area.

Preface
List of Abbreviations
Chapter 1. Practical Considerations in Mechanochemical Organic Synthesis
- 1.1. A Historical Perspective
- 1.2. Modern Laboratory Instrumentation for Mechanosynthesis
- 1.3. Contamination From Wear in Organic Mechanosynthesis
- 1.4. Analysis and Monitoring of Mechanochemical Reactions
Chapter 2. Carbon–Carbon Bond- Forming Reactions
- 2.1. Heck Coupling
- 2.2. Suzuki Coupling
- 2.3. Sonogashira Coupling
- 2.4. Glaser Coupling
- 2.5. Michael Reaction
- 2.6. Aldol Condensation
- 2.7. Morita–Baylis–Hillman Reaction
- 2.8. Knoevenagel Condensation
- 2.9. Barbier Allylation
- 2.10. Gewald Reaction
- 2.11. Pinacol Reaction
- 2.12. Grignard and McMurry Reactions
- 2.13. Grignard–Zerewitinoff-Like Reaction
- 2.14. Wittig Reaction
- 2.15. Horner–Wadsworth–Emmons Reaction
- 2.16. Asymmetric Alkylation
- 2.17. Olefin Cross-Metathesis
- 2.18. Cross-Dehydrogenative Coupling
- 2.19. Reformatsky Reaction
- 2.20. Cascade Reactions
- 2.21. Arylaminomethylation
- 2.22. Naphthopyran Synthesis
Chapter 3. Carbon–Nitrogen Bond-Formation Reactions
- 3.1. 1,2-Dione/Diamine Condensation
- 3.2. Synthesis of Imines
- 3.3. Synthesis of (Thio)semicarbazones
- 3.4. Synthesis of Oximes
- 3.5. Synthesis of Hydrazones
- 3.6. Synthesis of Azines
- 3.7. Amide and Thioamide Bond Formation
- 3.8. Synthesis of Nitrones
- 3.9. Synthesis of Enamines and Enamine Ketones
- 3.10. Alkylation of Nitrogen
- 3.11. Synthesis of Biguanides and Guanidines
- 3.12. Additions to Double and Triple Bonds
- 3.13. Substitution Reactions
- 3.14. N-Arylation of Amines
- 3.15. Biginelli Reaction
- 3.16. Nitroso Bond Formation/Dissociation
Chapter 4. Carbon—Oxygen and Other Bond-Formation Reactions
- 4.1. C—O Bond Formation Reactions
- 4.2. Sulfur Bond Formation Reactions
- 4.3. Halogen Bond Formation Reactions
- 4.4. Phosphorus Bond Formation Reactions
- 4.5. Boron Bond Formation Reactions
- 4.6. Silicon Bond Formation Reactions
- 4.7. Bismuth Bond Formation Reactions
- 4.8. C—H Bond Formation: Hydrogenation
- 4.9. Multistep Mechanochemical Reaction
Chapter 5. Cycloaddition Reactions
- 5.1. Diels–Alder Reaction
- 5.2. 1,3-Dipolar Cycloadditions
Chapter 6. Oxidations and Reductions
- 6.1. Oxidations
- 6.2. Reductions
Chapter 7. Applications of Ball Milling in Nanocarbon Material Synthesis
- 7.1. Functionalization of Fullerenes
- 7.2. Functionalization of Single-Walled Carbon Nanotubes
- 7.3. Functionalization of Graphenes
Chapter 8. Applications of Ball Milling in Supramolecular Chemistry
- 8.1. Rotaxanes
- 8.2. Complexation of Fullerenes
Chapter 9. Experiments for Introduction of Mechanochemistry in the Undergraduate Curriculum
- 9.1. Green Chemistry at the University Level
- 9.2. Selected Experiments
Author Index
Subject Index

Davor Margetic

Dr. Davor Margetić is senior research scientist and acting head of the division of organic chemistry and biochemistry at Ruđer Bošković research Institute in Zagreb, Croatia. He is the head of the laboratory for physical organic chemistry and Professor of physical organic chemistry at Rijeka University.He graduated with a degree in chemical engineering at Zagreb University and continued in the field of organic syntheses with Ms.Sc. and Ph.D. studies in the field of theoretical and physical organic chemistry (Zagreb). The completion of his Ph.D. was followed by a postdoctoral research studies at the Centre for Molecular Architecture, Central Queensland University, Australia. There he worked with Professors Ronald Warrener and Doug Butler for 9 years (synthetic organic and computational chemistry). In 2002, he returned to Croatia to take up a position at RBI, and in 2009 he was promoted to senior research scientist (an equivalent of full professor at the university). Research interests of Dr. Margetić include the synthesis and investigation of theoretically interesting molecules, the study of reaction mechanisms, computational organic chemistry, and the development of environmentally-friendly organic reactions using novel techniques (extreme high pressures, microwave irradiation, and mechanochemistry). During his scientific career, Dr. Margetić has published 90 research papers, 42 electronic conference papers, and 9 book chapters. He has authored one book: "Microwave Assisted Cycloaddition Reactions" with Nova Science Publishers, New York (2011); and edited two books: Croatica Chemica ActA Special issue dedicated to the 70th birthday of Professor Z. B. Maksić (2009), and Special issue dedicated to 70th birthday of Professor M. Eckert-Maksić (2014).

Affiliations and expertise

Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička, Zagreb, Croatia

VŠ

Vjekoslav Štrukil

Dr. Vjekoslav Štrukil is a research associate at the laboratory for Physical Organic Chemistry at Rudjer Bošković Institute in Zagreb, Croatia. He obtained his B.Sc. (2005) and Ph.D. (2010) degrees from the Faculty of Science, University of Zagreb, Croatia. During several short visits to the Department of Chemistry, Cambridge University, United Kingdom (2009-2011), Dr. Štrukil started research in mechanochemistry and continued his training as a postdoctoral fellow at the Department of Chemistry, McGill University in Montreal, Canada, (2012-2013) working under the supervision of Professor Tomislav Friščić. In 2013, he received the Annual Award for Junior Researchers in Croatia. Apart from organic mechanochemistry, his scientific interests also include the synthesis and reactivity of guanidine and polyguanide derivatives, theoretical and experimental study of their physico-chemical properties, and the application of green synthetic methods in organic chemistry. Dr. Štrukil has co-authored 21 scientific papers.

Affiliations and expertise

Ruder Boškovic Research Institute, Zagreb, Croatia