Reactions and Syntheses In the Organic Chemistry Laboratory

by Tietze, Lutz F.; Eicher, Theophil; Diederichsen, Ulf; Speicher, Andreas; Schü; tzenmeister, Nina

• ISBN13: 9783527338146
• ISBN10: 3527338144
• Edition: 2nd
• Format: Paperback
• Copyright: 2015-06-22
• Publisher: Wiley-VCH

Summary

The second edition of this classic text book has been completely revised, updated, and extended to include chapters on biomimetic amination reactions, Wacker oxidation, and useful domino reactions.

The first-class author team with long-standing experience in practical courses on organic chemistry covers a multitude of preparative procedures of reaction types and compound classes indispensable in modern organic synthesis. Throughout, the experiments are accompanied by the theoretical and mechanistic fundamentals, while the clearly structured sub-chapters provide concise background information, retrosynthetic analysis, information on isolation and purification, analytical data as well as current literature citations. Finally, in each case the synthesis is labeled with one of three levels of difficulty.

An indispensable manual for students and lecturers in chemistry, organic chemists, as well as lab technicians and chemists in the pharmaceutical and agrochemical industries.

Author Biography

Lutz F. Tietze studied chemistry at the universities of Freiburg and Kiel, Germany, and obtained his doctorate under the supervision of Prof. B. Franck in 1968 in Kiel. He then worked as a research associate with Prof. G. Büchi at MIT, Cambridge, USA, as well as with Prof. A. Battersby in Cambridge, UK. Since 1978 he has been Professor and Head of the Institute of Organic and Biomolecular Chemistry at the Georg-August-University in Göttingen, Germany. He has received many prizes, e.g. the highly prestigious Emil Fischer Medal of the German Chemical Society and has been awarded in 2012 with the position of a Distinguished Research Professor. His research focuses on the development of efficient and selective synthetic methods, combinatorial chemistry, the total synthesis of natural products and the design of new selective anticancer agents. He has over 460 papers, 34 patents and four books to his name.

Theophil Eicher studied chemistry at the University of Heidelberg, Germany, and obtaind his Ph.D. under Georg Wittig in 1960. After postdoctoral work at Columbia University, New York, USA, in the laboratories of Ronald Breslow, he habilitated 1967 at the University of Würzburg, Germany, under Siegfried Hünig. In 1974 he was appointed as Associate Professor at the University of Hamburg, in 1976 as Full Professor of Organic Chemistry at the University of Dortmund, Germany. Since 1982, he worked as Full Professor at the University of the Saarland, Germany, and was retired in 2000. His research interests concerned the synthetic chemistry of cyclopropenones and triafulvenes, as well as natural product synthesis in the field of bryophyte constituents. He is co-author of several books. Jointly with L. F. Tietze, he was awarded the literature prize of the "Fonds der chemischen Industrie". He is Dr. h. c. and Prof. a. h. of the Facultad de Quimica of the Universidad de la Republica, Montevideo/Uruguay.

Ulf Diederichsen studied Chemistry in Freiburg, Germany, with a diploma work in organic synthesis and completed his Ph.D. in 1993 under the supervision of Albert Eschenmoser at the ETH Zürich working on homo- and glucose-DNA. Following postdoctoral work on radical chemistry at the University of Pittsburgh, USA, in the group of Dennis Curran, he gained his habilitation at the Technical University Munich, Germany, with Horst Kessler as mentor. In 1999, he was appointed professor of Organic Chemistry at the University Würzburg, Germany, until joining the Georg-August-University in Göttingen, Germany, in 2001 as full professor of Organic Chemistry. He was visiting professor at the LMU Munich and Goering Visiting Professor at the University of Wisconsin, USA. In 1999 he got the Karl Winnacker stipend and Hellmut-Bredereck award and is an ordinary member of Göttingen Academy of Sciences and Humanities since 2012.

Andreas Speicher studied chemistry at Saarland University,Germany. He obtained his Ph.D. in 1994 under Theophil Eicher and was honoured with the Eduard-Martin-Award of his university. He started his independent scientific career and completed habilitation in 2003 (Privatdozent). He is head of a research group and university lecturer for organic chemistry at the Saarland University and was appointed extraordinary professor in 2011. He is temporary holding a guest professorship at the University of Strasbourg/France since 2006 and is co-author of several books. His research interests are directed to synthesis and characterization of chemically and biologically relevant natural products, especially to axially chiral macrocyclic compounds.

Table of Contents

C-C BOND FORMATION
Nucleophilic Addition to Aldehydes, Ketones, Carboxylic Acid Derivatives (Esters, Anhydrides) and alpha,beta-Unsaturated Carbonyl Compounds;
Carbonyl Olefination
Alkylation of Aldehydes/Ketones, Carboxylic Acids, and beta-Dicarbonyl Compounds
Reactions of the Aldol and Mannich Type
Electrophilic and Nucleophilic Acylation
Reactions of Alkenes via Carbenium Ions
Transition-Metal-Catalyzed Reactions
Pericyclic Reactions
Radical Reactions

OXIDATION AND REDUCTION
Epoxidation of C=C Bonds
Dihydroxylation of C=C Bonds
Oxidation of Alcohols to Carbonyl Compounds
Enantioselective Reduction of Ketones
Biomimetic Reductive Amination
Enantioselective Wacker

HETEROCYCLIC COMPOUNDS
Three- and Four-Membered Heterocycles
Five-Membered Heterocycles
Six-Membered Heterocycles
Condensed Heterocycles
Other Heterocyclic Systems;
Heterocyclic Dyes

SELECTED NATURAL PRODUCTS
Isoprenoids
Carbohydrates
Amino Acids and Peptides
Nucleotides and Oligonucleotides

DOMINO REACTIONS
Domino Reactions in Synthetic Methodology
Domino Reactions in The Synthesis of Alkaloids
Domino Reactions in The Synthesis of Isoprenoids
Domino Reactions for The Synthesis of Chromans And Dioxins
Domino Reactions in The Synthesis of Chiroptical Switches

INDEX OF REACTIONS
INDEX OF PRODUCTS
SUBJECT INDEX