E-Book Overview
The replacement of hydrogen with fluorine in organic molecules can profoundly influence their chemical and physical properties, leading to a range of compounds with highly desirable properties. These molecules are of interest across the wide spectrum of industrial and academic organic chemistry, so that organofluorine chemistry is economically highly important.
Organofluorine Chemistry will help chemists to develop a systematic knowledge of the chemistry of fluorine with a view towards its application in the design of new reactions and syntheses, and the creation of novel fluorinated molecules and materials. With initial chapters focusing on why fluorine creates such unique properties in organic compounds, the book then covers general reactions of fluorine. Coverage is chosen from the recent research literature, concentrating on the development of novel bioactive compounds and catalytic ligands, and explaining, in the context of the initial chapters, how and why fluorine is so effective. With a final chapter covering the general synthetic chemistry of organofluorine compounds, the book is a cohesive summary of the fundamental principals of organofluorine chemistry.Content: Chapter 1 Fundamentals in Organic Fluorine Chemistry (pages 1–100): Chapter 2 Unique Reactions Incluced by Fluorine (pages 101–138): Chapter 3 Reactions Activated by a Strong Interaction Between Fluorine and Other Atoms (pages 139–172): Chapter 4 Hydrogen Bonding in Organofluorine Compounds (pages 173–185): Chapter 5 Fluorinated Ligands for Selective Catalytic Reactions (pages 186–205): Chapter 6 Fluorine in Drug Designs (pages 206–222): Chapter 7 Method for Introduction of Fluorine?Functionality Into Molecules (pages 223–336):
E-Book Content
Organofluorine Chemistry
Organofluorine Chemistry
Kenji Uneyama Professor, Department of Applied Chemistry, Okayama University, Japan
C 2006 K. Uneyama
Blackwell Publishing Ltd Editorial Offices: Blackwell Publishing Ltd, 9600 Garsington Road, Oxford OX4 2DQ, UK Tel: +44 (0) 1865 776868 Blackwell Publishing Professional, 2121 State Avenue, Ames, Iowa 50014-8300, USA Tel: +1 515 292 0140 Blackwell Publishing Asia Pty, 550 Swanston Street, Carlton, Victoria 3053, Australia Tel: +61 (0)3 8359 1011 The right of the Author to be identified as the Author of this Work has been asserted in accordance with the Copyright, Designs and Patents Act 1988. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by the UK Copyright, Designs and Patents Act 1988, without the prior permission of the publisher. First published 2006 by Blackwell Publishing Ltd ISBN-13: 978-14051-2561-1 ISBN-10: 1-4051-2561-6 Library of Congress Cataloging-in-Publication Data is available A catalogue record for this title is available from the British Library Set in 10/12pt Minion & Optima by TechBooks, New Delhi, India Printed and bound in India by Replika Press Pvt, Ltd, Kundli The publisher’s policy is to use permanent paper from mills that operate a sustainable forestry policy, and which has been manufactured from pulp processed using acid-free and elementary chlorine-free practices. Furthermore, the publisher ensures that the text paper and cover board used have met acceptable environmental accreditation standards. For further information on Blackwell Publishing, visit our Web site: www.blackwellpublishing.com
Contents
Preface
ix
1
1 1
2
Fundamentals in Organic Fluorine Chemistry 1.1 Some physical properties of organic fluorine compounds 1.1.1 Effect of the fluorine atom on the molecular orbital energy levels of organic molecules and refractive inde