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Lutz F. Tietze - Reactions and Syntheses: In the Organic Chemistry Laboratory

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Lutz F. Tietze Reactions and Syntheses: In the Organic Chemistry Laboratory

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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.

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The Authors

Prof. Dr. Lutz F. Tietze

Georg-August-University Gttingen

Institute of Organic and Biomolecular Chemistry

Tammannstr. 2

37077 Gttingen

Germany

Prof. Dr. Theophil Eicher

Saarland University

Campus B6.1

66123 Saarbrcken

Germany

Prof. Dr. Ulf Diederichsen

Georg-August-University Gttingen

Institute of Organic and Biomolecular Chemistry

Tammannstr. 4

37077 Gttingen

Germany

Prof. Dr. Andreas Speicher

Saarland University

FR 8.1 - Organic Chemistry

Campus C4.2

66041 Saarbrcken

Germany

Dr. Nina Schtzenmeister

University of Bristol

School of Chemistry

Cantock's Close

Bristol, BS8 1TS

UK

Cover

The cover image was kindly supplied by Professor Lutz F. Tietze.

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

Library of Congress Card No.: applied for

British Library Cataloguing-in-Publication Data

A catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at .

2014 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form by photoprinting, microfilm, or any other means nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

Print ISBN: 978-3-527-33814-6

ePDF ISBN: 978-3-527-68872-2

ePub ISBN: 978-3-527-68874-6

Mobi ISBN: 978-3-527-68873-9

Preface to the First Edition
1 Background

The book Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium was first published in German in 1981, with a second edition in 1991, and was translated into Japanese in 1984 (second edition 1995), English in 1989, Chinese in 1999, Russian in 2000, and Korean in 2002. The intention was

  • to associate classes of compounds and functionalities with reaction types and mechanisms,
  • to offer a great number of reliable preparative procedures of general importance, and
  • to show the usefulness and robustness of the offered procedures for the synthesis of selected interesting compounds of relevance in biology, pharmacy, and medicine.

Since the last German edition, many new preparative procedures have been developed showing high chemo, regio, diastereo, and enantioselectivity, which frequently approach the selectivity of enzymatic transformations with the advantage of lower substrate specificity. In addition, new methods such as combinatorial chemistry, solid-phase chemistry, high-pressure chemistry, and the use of microwaves for heating have been introduced. Moreover, the efficiency of a synthesis, which can be defined as the increase in complexity per transformation, the avoidance of toxic reagents and solvents, and the preservation of resources are important issues in modern preparative organic chemistry. Significant developments in the last years have been realized in transition-metal catalysis, organocatalysis, and domino reactions. This progress has been impressively documented in Classics of Total Synthesis [1], Organic Synthesis Highlights [2], and Domino Reactions in Organic Synthesis [3].

As a consequence, we now present this book Reactions and Syntheses in the Organic Chemistry Laboratory in a new form with respect to its concept and organization and extensively renewed with respect to its content.

Its major highlights are as follows:

  1. The basic units as well as the main objectives are syntheses (up to multistep syntheses with more than five steps) of interesting and instructive target molecules from various fields of organic chemistry. Each synthesis is centered around one or more methods and reaction principles of general synthetic relevance.
  2. As before, the users of the new book are provided with carefully elaborated experiments, which are described in preparative and analytical detail. However, experiments and syntheses are accompanied throughout in concentrated form by the required general, theoretical, and mechanistic background and explanations. Special attention is given to retrosynthetic analysis and alternative approaches of synthesis for a given target molecule.
  3. To allow the inclusion of a representative and qualified spectrum of contemporary synthetic methods, more than 70% of the content of the former book has been replaced by more recent and more relevant experimental examples. The remaining (older) syntheses have been updated with respect to description of their general background.

Considering the various types of users of the book in the past, there has been a definite and broad acceptance among chemists and pharmacists on a more advanced level, besides graduate students and researchers in universities and industry. From these considerations, the following consequences have emerged for the third edition:

  • General laboratory information, such as safety, first aid, performance of chemical reactions, instrumentation and standard apparatus, and isolation and purification of products, has been omitted. Methods for the formation and transformation of basic functional groups in organic compounds, regarded as important at the elementary education level in organic laboratory practice, are not described. These topics are comprehensively covered in other relevant textbooks [46].
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