Synthetic Organic Sonochemistry

447 Pages·1998·19.438 MB·English

by  Jean-Louis Luche (auth.)

SYNTHETIC ORGANIC
SONOCHEMISTRY
SYNTHETIC ORGANIC
SONOCHEMISTRY
JEAN-LOUIS LUCHE
Laboratoire de Chimie Moleculaire et Environment
Universite de Savoie-ESIGEC
Le Bourget du Lac, France
with the assistance of
CLAUDIA BIANCHI
MICHEL CHANON
I'EDROCINTAS
ERIC CORDEMANS
HOUDA FILUON
THIERRY LEPOINT
FRAN<;:OISE LEPOINT-MULLIE
ANDRE LoUPY
TIMOTHY J. MASON
CHRISTIAN PETRIER
VmoRlo RAGAINI
DAVID WALTON
Springer Science+Business Media, LLC
L1brary of Congress Cataloging-in-Publ ieation Data
Luehe, Jean-Lou i s.
Synthet i c organ j c sonochem i stry / Jean-Lou 1s Luche.
p. em.
Ine I udes bi b li ograph i ea I referenees and indexes.
ISBN 0-306-45916-7
1. Sonochem i stry. 2. Organ i c campounds--Synthes i s. 1. Title.
QD801.L83 1998
547' .13--de21 98-20264
CIP
ISBN 978-1-4899-1912-0 ISBN 978-1-4899-1910-6 (eBook)
DOI 10.1007/978-1-4899-1910-6
© 1998 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1988.
Softcover reprint of the hardcover I st edition 1988
http://www.plenum.com
109 8765432 1
All rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form
or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise,
without written permission from the Publisher
THE AUTHORS
Thierry Lepoint and Fran~oise Lepoint-Mullie
Laboratoire d'Etude de la Cavitation, Institut Meurice-Chimie,
Avenue E. Gryzon 1, 1070 Bruxelles, Belgium.
Jean-Louis Luche and Christian Petrier
Laboratoire de Chirnie Moleculaire et Environnement,
Universite de Savoie-ESIGEC, 73376 Le Bourget du Lac, France.
Houda Fillion
Laboratoire de Chirnie Organique, Universite Claude Bemard de Lyon,
Faculte de Pharmacie, 8 Avenue RockefeIler, 69373 Lyon Cedex 08, France.
Andre Loupy
Laboratoire des Reactions Selectives sur Support, Bat. 410,
Universite Paris-Sud, 91405 Orsay Cedex, France.
Pedro Cintas
Departamento de Qufmica Organica,
Universidad de Extremadura, 06071 Badajoz, Spain.
Claudia L. Bianchi and Vittorio Ragaini
Dipartimento de Chimica Fisica ed'Elettrochimica,
Universita degli Studi di Milano, Via Golgi 19,20133 Milano, Italy.
Timothy'. Mason and David J. Walton
School of Natural and Environmental Sciences, Coventry University,
Priory Street, Coventry CV1 5FB, United Kingdom.
Eric Cordemans de Meulenaer
UNDATIM, 7 rue du Bosquet, Louvain la Neuve, Belgium.
Michel Chanon
Laboratoire SM3B, Universite Aix-Marseille 3, Faculte Saint-Jerome D12,
Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France.
PREFACE
TEAN-LOUIS LUCHE
A French poet
of this eentury, Pierre Mae Orlan, wrote "Adventure does not
exist, it is only in the mind of he who is pursuing it, and, as soon as it is at one's
finger tips, it vanishes to come back to life, far away, in a different shape, at the
frontiers of imagination".
This sentence could be used to define the adventure that many sonochemists
experienced. Most of them did not even suspect that the "laboratory trick" they
were using was the first contact with a considerable amount of science.
If a personal note is allowed here, it ean be interesting to mention the part played
by chance in my involvement in sonochemistry. Almost 20 years ago, we had to
perform an apparently simple Grignard reaetion with n-butylmagnesium
bromide and geranial, but the results were repeatedly unsatisfactory. The one-pot
Barbier technique was attempted, also without success. From my studies at the
University, I imagined that the failure of the latter reaction could be caused by a
common phenomenon known by solid state chemists as passivation, which in
some cases can be overcome by ultrasonication. By chance, an ultrasonie bath was
sitting on the next beneh, borrowed to clean some equipment. We clamped our
reluctant reaction mixture into the bath, the reaction proceeded vigorously, and ...
the adventure started. Without knowing anything about cavitation, high
energies, ete., we had an illustration of Goethe's word "Am Anfang war die Tat"
(at the Beginning was the Act).
What motivated many sonochemists when they started their work was certainly
curiosity, and the desire, inherent to seientific work, to leam more from the
unknown. At the present time, they should not be disappointed, since sono
ehemistry has shown unexpected links with so many domains of science: physics,
acoustics, plasmas, high energy states (adventures far from chemistry), and is
applied in inorganic chemistry, polymers, materials science, biology, various
processes of engineering, and the object of this work, organic synthesis.
VIII SYNTHETIC ORGANIC SONOCHEMISTRY
A number of books have been published,l most of which are mentioned in the
following ehapters. They provide general views on the various domains of
applieation by the way of specialized eontributions devoted, for example, to
theories, materials scienees, biology, organic and inorganie synthesis, metallurgy,
ete. Many reviews with either a general seope or limited to specific aspeets are
available in many languages, giving the reader direct aeeess to sonoehemical
applieations in his mother tongue.2 The list below is not exhaustive, and a
number of other titles are quoted in other parts of this book.
From a literature survey, it appeared that, with only the exeeption of a short book
published in 1989,3 no work specifieally dedicated to organie synthesis, one of the
major fields of sonoehemistry, had been published. This prompted the present
work to be undertaken, especially beeause during the last 15 years, a large number
of articles have been published, eovering most aspeets of organic reaetions and
methodologies. Besides the aspeet of bringing together data from the literature,
most often seattered among many journals,4 the present work also eonstituted a
good opportunity to present results that were less weIl understood, eontroversial,
or· simply not interpreted at all.
A seeond, and probably more important point is to show that, if sonoehemistry is
a really difficult topic from a theoretieal point of view, in many eases it offers a
very simple solution to synthetie problems. Provided a minimum easy-to-get
praetieal knowledge is aequired, sonoehemical methods ean be used in most
laboratories without the need for expensive equipment, and it is by no means a
1 (a) Margulis, M.A. Ultrasonic Reacfions and Sonoluminescence Khimia, Moscow, 1986 (in
Russian); (b) Mokry, E.N.; Starchevskii, V.L. Ultrasound in Oxidative Processes with Organic
Substances Lvov (Ukraine) 1987 (in Russian); (c) Ultrasound, Its Chemical, Physical and
Biological Effects (Suslick, K.S. Ed.), VCH, Weinheim, 1988; (d) Mason, T.J.; Lorimer, J.P.
Sonochemistry, Theory, Applications and Uses 0/ Ultrasound in Chemistry Ellis Horwood,
Chichester, 1988; (e) Advances in Sonochemistry (Mason, T.J. Ed.), JAI Press, London, 1990,
Vol. 1; 1991, Vol. 2; 1993, Vol. 3; 1996, Vol. 4; (f) Mason, T.J. Practical Sonochemistry Ellis
Horwood, Chichester, 1991; (g) Current Trends in Sonochemistry (Price, G.J. Ed.), The Royal
Society of Chemistry, Oxford, 1992; (h) Margulis, M.A. Sonochemistry and Cavitation Gordon
and Breach, London, 1995.
2 (a) Boudjouk, P. J. Chem. Ed. 1986,63,427-429; (b) Suslick, K.S. Adv. Organomet. Chem.1986,
25,73-119; (c) Jitai, L; Yuhua, W. Huaxue Shiji, 1987, 9, 98-102 (in Chinese); (d) Kimura, T.;
Ando, T. Yuki Gosei Kagaku Kyokaishi 1988, 46, 1124-1133 (in Japanese); (e)Rehorek, D.;
Schöffauer, 5.; Hennig, H. Z. Chem. 1989,29,389-396 (in German); (f) Suslick, K.S. Scientific
American Feb. 1989, 80-86; (g) Einhorn, c.; Einhorn, J.; Luche, J.L. Synthesis 1989,787-813; (h)
Goldberg, Yu.; Sturkovich, R.; Lukevics, E. Heterocydes 1989, 29, 597-627; (i) De Souza
Barboza, J.c.; Aarao Serra, A. Quimica Nova 1992, 15, 302-315 (in Portuguese); G) Mornstein, V.;
Kaplan, P. Chem. Listy 1994,88, 650-659; (k) Serpone, N.; Colarusso, P. Res. Chem. Intermed.
1994,20, 635-679; (1) Pestman, J.M.; Engberts, J.B.F.N.; de Jongh, F. Red. Trav. Chim. Pays Bas
1994,113, 533-542; (m) Shvekhgheimer, G.A. Khim. Geterosikl. Soedin.1994, 723-755 (in
Russian); (n) Peters, D.; Miethchen, R. J. prakt. Chem. 1995,337,615-627; (0) Peters, D. J. Mater.
Chem. 1996,6, 1605-1618.
3 Ley, S.V.; Low, C.M.R. Ultrasound in Synthesis Springer Verlag, Berlin, 1989.
4 Since 1994, a journal specifically dedicated to sonochemistry has been published (Ultrasonics
Sonochemistry, Butterworth, then Elsevier).
PREFACE IX
domain restricted to experts only. Practitioners who encounter problems at the
bench should, however, find it advantageous to read some theory, without
mathematics, to understand more of what can be expected than obtained, in
terms of success or failure. The first chapter should also help in acquiring a
physical "feeling" of what an acoustic wave is, and what can be expected from it.
At the other extreme, industrial chemists will find reflections on how to
undertake larger scale experiments in Chapter 8.
Between these, the organic chemist can find examples and, hopefully, new ideas,
in the various chapters directly related to this domain. Enthusiasm for new
possibilities should, however, be tempered by reflection, since even if
sonochemical methods have proved their efficiency, no panacea exists,
fortunately for the experimentalist who will continue to have the possibility of
demonstrating scientific skills through exploration.
Thanks are due to the colleagues who agreed to participate in the refereeing
committee, namely, Professors T. Ando (University of Shiga, Japan), c. Dupuy
(University of Grenoble, France), and R. Miethchen (University of Rostock,
Germany). By their comments and corrections, they contributed greatly to the
improvement of the manuscript.
The numerous discussions held during informal meetings and the Conferences
of the European Society of Sonochemistry with distinguished sonochemists,
greatly helped in the advancement of the difficult rationalization of the newborn
sonochemistry. Among others should be mentioned the names of:
A. Campos Neves (Universidade de Coimbra, Portugal), G. Descotes (Universite
de Lyon, France), M. Lie Ken Jie (University of Hong Kong), J.P. Lorimer
(Coventry University, UK), M.A. Margulis (All-Russia Institute of Organic
Chemistry, Moscow, Russia), A. Mourino (Universidad de Santiago, Spain),
G. Portenlänger (Universität München, Germany), G. Price (University of Bath,
UK), L. Sarandeses (Universidad de La Corufta, Spain), K.S. Suslick (University of
Illinois at Urbana-Champaign, USA), S. Toma (Comenius University, Bratislava,
Slovakia), M. Vinatoru (C.D. Nenitzescu Institute of Organic Chemistry,
Bucharest, Romania).
Special thanks are due to Professor G. Reverdy, University of Savoie at
Chambery, France, and to the staff of Grenoble Sciences, particularly Professor
J. Bornarel, N. Sauval, and S. Bordage.
TAßLE OF CONTENTS
Chapter 1 - Theoretical Bases .......................................................................... 1
Thierry Lepoint and Fran~oise Lepoint-Mullie
1. UItrasonic Waves .................................................................................................. 3
1.1. Frequency ............................................................................................................. 3
1.2. Acoustic Intensity................................................................................................. 4
1.3. Generation of Ultrasonic Pressure Waves.............................................................. 5
1.4. Propagation of Ultrasound.................................................................................... 6
1.5. Attenuation.......................................................................................................... 7
1.6. Radiation Press ure, Streaming, and Microstreaming ............ ................................. 8
1.7. Spatial Distribution of the Sound Field............................................................... 11
1.8. Measurements of Acoustic Intensity....................................................................... 12
1.8.1. The calorimetric method ............................................................................ 13
1.8.2. The radiometrie method............................................................................. 13
1.8.3. Measurements with hydrophones................................................................ 14
2. Cavitation Inception, Nucleation...................................................................... 15
2.1. The Process of NucIeation..................................................................................... 15
2.1.1. Statement of the problem........................................................................... 15
2.1.2. The crevice model....................................................................................... 17
2.2. The Concept of Threshold ............................................ ...... .................................. 19
2.2.1. The Blake threshold.................................................................................. 19
2.2.2. A word about the Minneart frequency ........ ................................................. 21
2.2.3. Rectified diffusion...................................................................................... 21
2.2.4. Transient cavitation ......................... .......................................................... 24
3. Bubble Dynamies.................................................................................................... 25
3.1. Isolated Bubbles and Their Collapse.................................................................... 25
3.1.1. The Rayleigh-Plesset equation................................................................... 25
3.1.2. Types of bubble behavior............................................................................ 28
3.2. Non-radial Oscillations (Rayleigh-Taylor instability) ....................................... 31
3.3. Bubbles Next to a Solid Wall: The Process of Erosion........................................... 32
3.3.1. Impact of liquid jets.................................................................................... 33
3.3.2. Emission of shock waves............................................................................. 36
3.4. Forces on Bubbles in aSound Field........................................................................ 36
3.4.1. Primary Bjerknes force................................................................................ 37
3.4.2. Secondary Bjerknes force............................................................................. 38
XII SYNTHETIC ORGANIC SONOCHEMISTRY
4. Bubbles as Aeoustic Emitters............................................................................... 41
4.1. Elements of an Acoustic Spectrum ......................................................................... 41
4.2. Chaotic Behavior, the Isolated Bubble................................................................ 42
4.3. Bubble Cloud (The passage towards transient cavitation)..................................... 44
5. How and Where Does the Chemie al Aetivity of Cavitation Start? ............ 45
6. Single Bubble Sonolumineseenee and Sonoehemistry................................. 46
0/
Chapter 2 - Sonochemistry Solutions.................................................... 51
Christian Petrier and Jean-Louis Luche
1. Sonoehemieal Reaetivity...................................................................................... 52
1.1. Sonochemical Switching....................................................................................... 52
1.2. An Attempted Rational View on Sonochemical Reactions .................................... 52
1.3. Parameters Influencing the Sonochemical Reactivity ............................ ............... 53
1.3.1. Frequency.................................................................................................... 53
1.3.2. Energy and temperature.............................................................................. 54
1.4. The Site of the Sonolytic Reaction....................................................................... 57
1.4.1. Reactions in the gas phase inside the bubble.............................................. 57
1.4.2. Reactions in the interfacial region.............................................................. 60
1.4.3. Reactions in the bulk liquid........................................................................ 62
2. Synthetic Applications.......................................................................................... 63
2.1. Processes Based on a Sonolytic Step...................................................................... 64
2.1.1. Sonolysis of the carbon-halogen bond.......................................................... 64
2.1.2. Sonolysis of the carbon-nitrogen bond.......................................................... 69
2.1.3. Sonolysis of hydrogen-element bonds.......................................................... 70
2.1.4. Sonolysis of transition metal complexes...................................................... 74
2.1.5. Other sonolyses .......................................................................................... 77
2.2. Non-sonolytic Reactions ....................................................................................... 78
2.2.1. Additions with C-C bond formation............................................................ 78
2.2.2. Formation and cieavage of carbon-heteroelement bonds ...................... ....... 82
2.3. Substitutions......................................................................................................... 85
2.3.1. Substitutions leading to C-C bonds .................. ...... .................. .................... 86
2.3.2. Substitutions leading to carbon-heteroelement bonds.. ...................... ........... 87
2.4. Redox Reactions........... ............ .................. .................. ..... ................................... 88
Chapter 3 - Cycloadditions .......... .............. .............................. ....................... 91
Houda Fillion and Jean-Louis Luche
1. Sonoehemical Cycloadditions............................................................................. 92
1.1. [2+2] Additions of Ketenes and Keteniminiums to Olefins..................................... 92
1.1.1. Cycioadditions of ketenes........................................................................... 92
1.1.2. Cycioadditions of keteniminiums................................................................ 93
1.2. [3+2] Additions..................................................................................................... 94
1.2.1. Nitrones and nitrile oxides as 1,3-dipoles................................................... 94
1.2.2. Azides as 1,3-dipoles.................................................................................. 96