Aza-crown Macrocycles (the Chemistry Of Heterocyclic Compounds, Volume 51)

Aza-Crown Macrocycles Jerald S. Bradshaw Krzysztof E. Krakowiak Reed M. Izatt JOHN WILEY & SONS This Page Intentionally Left Blank AZA-CROWN MACROCYCLES Thir i\ [hc. FiJwFirsr Volume in thP Serrc.? THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS A SERIES OF MONOGRAPHS EDWARD C. TAYLOR, Editor ARNOLD WEISSBERGER, Founding Editor AZA=CROWN MACROCYCLES Jerald S. Bradshaw Krzysztof E. Krakowiak Reed M. Izatt Department of Chemistry Brigham Young University Provo. Utah 84602-1022 AN INTEKSCIENCE PUBLICATION John Wiley & Sons, Inc. NEW YORK - CHICHESTER BRISBANE TORONTO SINGAPORE This text is printed on acid-free paper. Copyright 0 1993 by John Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada Reproduction o r translation of any part of this work beyond that permitted by Section 107 o r 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful. Library of Congress Cataloging in Publication Data: Bradshaw. J. S . Aza-crown macrocycles / Jerald S. Bradshaw, Krzysztof E. Krakowiak. Reed M. Izatt. p. cm. -- (The Chemistry of heterocyclic compounds) Includes index. ISBN 0-471-52485-9 1. Macrocyclic compounds. 2. Crown ethers. 3. Organonitrogen compounds. I. Krakowiak, Krzysztof E. 11. Izatt, Reed McNeil, 1926. 111. Title. IV. Series. QD401.B77 1993 547’.59--dc20 92-35450 The Chemistry of Heterocyclic Compounds Introduction to the Series The chemistry of heterocyclic compounds constitutes one of the broadest and most complex branches of chemistry. The diversity of synthetic methods utilized in this field, coupled with the immense physiological and industrial significance of heterocycles, combine to make the general heterocyclic arena of central importance to organic chemistry. The Chemistry of Heterocyclic Compounds, published since 1950 under the initial editorship of Arnold Weissberger, and later, until Dr. Weissberger’s death in 1984, under our joint editorship, has attempted to make the extraordinarily complex and diverse field of heterocyclic chemistry as organized and readily accessible as possible. Each volume has dealt with syntheses, reactions, properties, structure, physical chemistry, and utility of compounds belonging to a specific ring system or class (e.g., pyridines, thiophcnes, pyrimidines, three-membered ring systems). This series has become the basic reference collection for information on heterocyclic compounds. Many broader aspects of heterocyclic chemistry are recognized as disciplines of general significance which impinge on almost all aspects of modern organic and medicinal chemistry, and for this reason we initiated several years ago a parallel series entitled Generul Heterocyclic Chemistry, which treated such topics as nuclear magnetic resonance, mass spectra, photochemistry of heterocyclic compounds. the utility of heterocyclic compounds in organic synthesis, and the synthesis of heterocyclic compounds by means of 1,3-dipolar cycloaddition reactions. These volumes are of interest to all organic and medicinal chemists, as well as to those whose particular concern is heterocyclic chemistry. It has become increasingly clear that this arbitrary distinction created as many problems as it solved, and we have therefore elected to discontinue the more recently initiated series General Heterocyclic Chemistry and to publish all forthcoming volumes in the general area of heterocyclic