1,4-Cycloaddition Reactions The Diels-Alder Reaction in Heterocyclic Syntheses - JAN HAMER.pdf

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ORGANIC
CHEMISTRY
Edited by
A SERIES OF MONOGRAPHS
A L F R E D T. B L O M Q U I S T
Department of Chemistry, Cornell University, Ithaca, New York
Volume 1.
Volume 2.
Volume 3.
Volume 4.
Volume 5.
Wolfgang Kirmse.
Brandes H. Smith.
Michael Hanack.
Donald J. Cram.
CARBENE CHEMISTRY. 1 9 6 4
BRIDGED AROMATIC COMPOUNDS. 1 9 6 4
CONFORMATION THEORY. 1 9 6 5
FUNDAMENTALS OF CARBANION
CHEMISTRY. 1 9 6 5
Kenneth B . Wiberg (Editor).
OXIDATION IN ORGANIC CHEMISTRY
PART A . 1 9 6 5
PART Β .
In
preparation.
Volume 6.
R . F . Hudson
STRUCTURE AND MECHANISM IN O R -
GANO-PHOSPHORUS CHEMISTRY. 1 9 6 5
Volume 7.
Volume 8.
A . William Johnson.
Jan H a m e r (Editor).
YLID CHEMISTRY. 1 9 6 6
1,4-CYCLOADDITION REACTIONS. 1 9 6 7
IN PREPARATION
M . P . Cava and M. J. Mitchell.
CYCLOBUTADIENE AND RELATED
COMPOUNDS
Henri Ulrich
CYCLOADDITION COMPOUNDS OF
HETEROCUMULENES
1,4-Cycloaddition Reactions
THE
DIELS-ALDER
REACTION
SYNTHESES
I N
HETEROCYCLIC
EDITED BY
JAN
HAMER
DEPARTMENT OF CHEMISTRY
TULANE UNIVERSITY
NEW ORLEANS, LOUISIANA
1967
ACADEMIC
PRESS
New York and London
COPYRIGHT © 1967, BY ACADEMIC PRESS INC.
ALL RIGHTS RESERVED.
NO PART OF THIS BOOK MAY BE REPRODUCED IN ANY FORM,
BY PHOTOSTAT, MICROFILM, OR ANY OTHER MEANS, WITHOUT
WRITTEN PERMISSION FROM THE PUBLISHERS.
A C A D E M I C PRESS I N C .
111 Fifth Avenue, N e w York, N e w York 10003
United Kingdom Edition published by
A C A D E M I C PRESS INC. (LONDON) L T D .
Berkeley Square House, London W . l
LIBRARY OF CONGRESS CATALOG CARD NUMBER : 64-26040
PRINTED IN THE UNITED STATES OF AMERICA
List of Contributors
Numbers in parentheses indicate the pages on which the authors' contributions begin.
Mushtaq A h m a d ,
Department of Chemistry, Tulane University, New Orleans,
Louisiana
(419)
R. L. Cobb,
Research and Development Department, Phillips
Petroleum
Company, Bartlesville, Oklahoma
(13)
J. Colonge,
University of Lyon, Lyon, France
(217)
G. Descotes,
University of Lyon, Lyon, France
(217)
Bernard T. Gillis,
Department of Chemistry, Duquesne University, Pittsburgh,
Pennsylvania
(143)
Klaus Gollnick,
Max-Planck-Institut fur Kohlenforschung, Abteilung Strahlen-
chemie, Miilheim-Ruhr, Germany
(255)
Jan Hamer,
Department of Chemistry, Tulane University, New Orleans, Louisiana
(1,205,419)
G. J. Janz,
Department of Chemistry, Rensselaer Polytechnic Institute, Troy,
New York
(97)
Gunter Kresze,
Organisch-Chemisches Institut, Technische Hochschule, Munich,
Germany
(453)
Manuel Lora-Tamayo,
Department of Organic Chemistry,
InstitutodeQuimica,
"Alonso Barba"
(C.5./.C.),
Madrid, Spain
(127, 179)
R. Madronero,
Department of Organic Chemistry, Instituto de Quimica,
"Alonso Barba" (C.S.I.C.), Madrid, Spain
(127)
G. Pfundt,
Max-Planck-Institut
fur Kohlenforschung, Abteilung
Strahlen-
chemie, Miilheim-Ruhr, Germany
(345)
Louis D. Quin,
Department of Chemistry, Duke University, Durham, North
Carolina
(47)
Gunther O. Schenck,
Max-Planck-Institut
fiir Kohlenforschung,
Abteilung
Strahlenchemie, Miilheim-Ruhr, Germany
(255, 345)
Jose L. Soto,
Department of Organic Chemistry, Instituto de Quimica, "Alonso
Barba"
( C . S . / . C ) ,
Madrid, Spain
(179)
S. D. Turk,
Research and Development Department, Phillips
Petroleum
Company, Bartlesville, Oklahoma
(13)
James A. Turner,
Department of Chemistry, Tulane University, New Orleans,
Louisiana
(205)
1
Present address: West Regional Laboratories, Pakistan Council of Scientific and
Industrial Research, Lahore, West Pakistan.
1
Preface
Detailed accounts of various aspects of the Diels-Alder reaction leading to
homocyclic systems have appeared in past years. The formation of heterocyclic
compounds by the same reaction has received scant attention despite the fact
that the use of an azo compound as a dienophile led to the generalization now
known as the Diels-Alder or 1,4-cycloaddition reaction.
It is the aim of this treatise to fill this lack, and to provide for the research
chemist or graduate student a ready source of information on 1,4-cyclo­
addition reactions leading to the formation of five- or six-membered hetero­
cyclic compounds.
An attempt has been made to present in each chapter an exhaustive and
critical survey of the 1,4-cycloaddition reaction under consideration. In order
to be of material value to the research chemist available data have been com­
piled in each chapter in the form of tables listing reaction conditions, yields,
products and some of their physical constants, and literature references. In
addition, each chapter is sufficiently detailed so that a chemist with little or no
knowledge of the subject would be able to understand and use it.
In Chapter 1 a brief survey is given of systems capable of 1,4-cycloaddition
reactions. This treatise is organized along the lines of the first chapter, which
thereby provides a bird's-eye view of the book.
JAN HAMER
vii

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