Catalysis of Organic Reactions CHEMICAL INDUSTRIES A Series ofReference Books and Textbooks Consulting Editor HEINZ HEINEMANN Heinz Heinemann, Inc., Berkeley, California Volume 1: Fluid Catalytic Cracking with Zeolite Catalysts, Paul B. Venuto and E. Thomas Habib, Jr. Volume 2: Ethylene: Keystone to the Petrochemical Industry, Ludwig Knie/, Olaf Winter, and Karl Stork Volume 3: The Chemistry and Technology of Petroleum, James G. Speight Volume 4: The Desulfurization of Heavy Oils and Residua, James G. Speight Volume 5: Catalysis of Organic Reactions, edited by William R. Moser Volume 6: Acetylene-Based Chemicals from Coal and Other Natural Resources, Robert J. Tedeschi Volume 7: Chemically Resistant Masonry, Walter Lee Sheppard, Jr. Volume 8: Compressors and Expanders: Selection and Application for the Process Industry, Heinz P. Bloch, Joseph A. Cameron, Frank M. Danowski, Jr., Ralph James, Jr., Judson S. Swearingen, and Marilyn E. Weightman Volume 9: Metering Pumps: Selection and Application, James P. Poynton Volume JO: Hydrocarbons from Methanol, Clarence D. Chang Volume 11 : Foam Flotation: Theory and Applications, Ann N. Clarke and David J. Wilson Volume 12: The Chemistry and Technology of Coal, James G. Speight Volume 13: Pneumatic and Hydraulic Conveying of Solids, 0. A. Williams Volume 14: Catalyst Manufacture: Laboratory and Commercial Preparations, Alvin B. Stiles Volume 15: Characterization of Heterogeneous Catalysts, edited by Francis Delannay Volume 16: BASIC Programs for Chemical Engineering Design, James H. Weber Volume 17: Catalyst Poisoning, L. Louis Hegedus and Robert W. McCabe Volume 18: Catalysis of Organic Reactions, edited by John R. Kosak Volume 19: Adsorption Technology: A Step-by-Step Approach to Process Evaluation and Application, edited by Frank L. Slejko Volume 20: Deactivation and Poisoning of Catalysts, edited by Jacques Oudar and Henry Wise Volume 21: Catalysis and Surface Science: Developments in Chemicals from Methanol, Hydrotreating of Hydrocarbons, Catalyst Preparation, Monomers and Polymers, Photocatalysts and Photovoltaics, edited by Heinz Heinemann and Gabor A. Somorjai Volume 22: Catalysis of Organic Reactions, edited by Robert L. Augustine Additional Volumes in Preparation Catalysis of Organic Reactions edited by Robert L. Augustine Department of Chemistry Seton Hall University South Orange, New Jersey MARCEL DEKKER, INC. New York • Basel Library of Congress Cataloging in Publication Data Main entry under title: Catalysis of organic reactions. (Chemical industries ; 22) Papers from the Tenth Conference on the Catalysis of Organic Reactions, held May 7-9, 1984, at Williamsburg, VA. Includes index. I. Chemistry, Organic-Synthesis-Congresses. 2. Catalysis-Congresses. I. Augustine, Robert L., [date). II. Conference on the Catalysis of Organic Reactions (I 0th : 1984 : Williamsburg, VA.) III. Series: Chemical industries ; v. 22. QD262.C35 1985 547.1'395 85-10242 ISBN 0-8247-7263-6 COPYRIGHT© 1985 by MARCEL DEKKER, INC. ALL RIGHTS RESERVED. Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilm- ing, and recording, or by any information storage and retrieval system, without permission in writing from the publisher. MARCEL DEKKER, INC. 270 Madison Avenue, New York, New York 10016 Current printing (last digit): IO 9 8 7 6 5 4 3 2 I PRINTED IN THE UNITED STATES OF AMERICA Preface About twenty years ago a group of individuals who were involved on a day to day basis with the application of catalytic processes to organic synthesis came together to establish a forum for the discussion of the practical aspects of catalysis in organic chemistry. The result was a conference held in June, 1966 on Catalytic Hydrogenation and Analogous Pressure Reactions,! sponsored by the New York Academy of Sciences and co-chaired by Joseph M. O'Connor of CIBA(presently CIBA-Geigy), Morris Friefelder of Abbot, and Melvin A. Rebensdorf of Upjohn. This conference was very successful and two years later in June, 1968, the Second Conference on Catalytic Hydrogenation and Analogous Pressure Reactions2 was held, chaired by Joseph O'Connor and again sponsored by the New York Academy of Sciences. The Third Conference3 (June, 1970), chaired by Melvin A. Rebensdorf and the Fourth Conference4 (September, 1972), chaired by Paul N. Rylander of Engelhard, were also sponsored by the New York Academy of Sciences despite the Academy's general policy of not sponsoring series of conferences in the same area, a fact which attests to the value of these conferences. At this stage, however, continuing Academy support for further conferences was not forthcoming so a small group of active participants in these previous meetings worked to independently sponsor the next iii iv Preface conference. This group called itself The Organic Reactions Catalysis Society and in the discussions leading to the formulation of a general policy for future meetings it became clear that the titles used for the first four conferences did not accurately describe the groups' changing interests. Thus, the Fifth Conference on Catalysis in Organic Synthesis5, co-chaired by Paul Rylander and Harold Greenfield of Uniroyal Chemical was held in Boston in April, 1975. A result of these conferences was the merging of the interests of the organic chemists with those of the catalytic chemists. Further evidence of this development came in 1975 with the affiliation of the Organic Reactions Catalysis Society (ORCS) with the North American Catalysis Society. The Sixth Conference on Catalysis in Organic Synthesis6, chaired by Gerard V. Smith of Southern Illinois University was held in Boston in May, 1976 in order to have the ORCS biennial conferences held in those years in which the biennial North American Catalysis Society National Meetings were not held. The Seventh Conference on Catalysis in Organic Synthesis?, chaired by William H. Jones of Merck Sharp and Dohme, was held in Chicago in June, 1978. Throughout this time the interests of the Society were expanding to include chemical processes and catalyst development. The Eighth Conference, chaired by William R. Moser of Worcester Polytechnic Institute and held in New Orleans in June, 1980, reflected this with a change in the conference title to Catalysis of Organic Reactions.8 The Ninth Conference on Catalysis of Organic Reactions,9 chaired by John R. Kosak of du Pont, was held in Charleston, SC in April, 1982. And that brings us to the present, the Tenth Conference on Catalysis in Organic Reactions held on May, 7-9, 1984, in Williamsburg, VA, which is the topic of this volume. It is obvious that the Organic Reactions Catalysis Society could not have reached this milestone without the enthusiastic support of a lot of people. Particular thanks must go to our "Founding Fathers" who worked so hard in the 1960's to get the first conferences established: Dale Blackburn of Smith Kline and French, Jack Campbell of Lilly, Morris Friefelder of Abbott, William Jones of Merck Sharp and Dohme, Joseph O'Connor of CIBA (now CIBA Geigy), William Pearlman of Parke-Davis (now Warner Lambert), Melvin Rebensdorf of Upjohn, Paul Rylander of Engelhard, William Selby of G.D. Searle, and David Wagner of Hoffman-LaRoche. Thanks must also go Preface V to the New York Academy of Sciences for its support during the formative years of the Society and to all of the Officers and Directors who have served over the years to develop the Society into what it is today. We cannot forget that without participants and speakers there would be no conferences and I would particularly like to thank our present speakers for taking the time out of their busy schedules to present aspects of their work and for being so cooperative in providing manuscripts of their talks so readily as to facilitate the publication of these proceedings. The financial support of this conference from the following corporations is gratefully acknowledged: Air Products and Chemicals, Allied Corporation, Chemical Data Systems, Degussa, E.I. du Pont de Nemours and Company, General Electric Company, W.R. Grace and Company, Hoffman-LaRoche, Merck Sharp and Dohme, The Procter and Gamble Company, Sandoz, G.D. Searle, Shell Development Company, Smith Kline and French, Standard Oil Company (SOHIO), Uniroyal Chemical, and Warner Lambert Company. The excellent job done by Jean DeRosa in preparing all of the manuscripts in this volume for publication is greatly appreciated. References I. Catalytic Hydrogenation and Analogous Pressure Reactions (J.M. O'Connor, ed.) Ann. N.Y. Acad. Sci., 145, Art. I, 1-206 (1967). 2. Second Conference .2!!. Catalytic Hydrogenation and Analogous Pressure Reactions (J.M. O'Connor, ed.), Ann. N.Y. Acad. Sci., 158, Art. 2, 439-588 (1969). 3. Third Conference .2!!. Catalytic Hydrogenation and Analogous Pressure Reactions (M.A. Rebensdorf, ed.), Ann. N.Y. Acad. Sci., 172, Art 9, 151- 276 (1970). 4. Fourth Conference on Catalytic Hydrogenation and Analogous Pressure Reactions (P.N. Rylander, ed.), Ann. N.Y. Acad. Sci., 214 (1973). 5. Catalysis in Organic Synthesis, 1976 (P.N. Rylander and H. Greenfield, eds.), Academic Press, New York, 1976. 6. Catalysis in Organic Synthesis, 1977 (G.V. Smith, ed.), Academic Press, New York, 1977.