Diazonium and Diazo Groups Volume 2 (1978).pdf

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The Chemistry
o
Diazonium and Diazo Groups
f
Edited by
Saul
Patai
Copyright
0
1978 by John Wiley
&
Sons Ltd.
All
rights reserved.
The
chemistry
of
diazonium
and
diazo
groups
Part
2
Edited
by
SAULPATAI
The
Hebrew
Utiiuersity, Jerusaletii
1978
JOHN
WILEY
&
SONS
CHICHESTER
-
N E W YORK
-
BRISBANE
-
TORONTO
An
In
ferscierice
61
Pttblicafioii
Copyright
@
1978
by
John Wiley
&
Sons Ltd.
Reprinted February
1979.
All
rights reserved.
N o
part
of
this book may bc reproduced by any means,
1
nor transmitted, nor translated into
; .
machine language
without the written permission
of
the publisher.
Library
of
Congress Catalog Card
No.
75-6913
ISBN
0 471 99492 8
(Pt.
I )
ISBN
0 471 99493 6
(Pt.
2)
ISBN
0
471
99415 4
(Set)
Printed in Great Britain
by
Page Bros (Norwich)
Ltd.
Mile Cross
Lane.
Norwich.
Contributing authors
W.
Ando
D.
A.
Ben-Efraim
C.
F.
Cooper
A.
J.
Fry
A.
F.
Hegarty
E. S. Lewis
G. Linstrumelle
J.
F.
McGarrity
J.
6.
Moffat
H.
M. Nienieyer
M.
Regitz
K.
Schank
R.
Shaw
P.
J.
Smith
S. Sorriso
V.
Sterba
K.
C.
Westaway
D.
Whittaker
D.
S.
Wulfman
Chemistry Department, The University of Tsukuba, Niiharigun,
Ibaraki
300-3
1,
Japan
The Weizmann Institute
of
Science, Rehovot, Israel
Department
of
Chemistry, University of Missouri-Rolla, Rolla,
Mo. 65401, USA
Wesleyan University, Middletoum, Connecticut, USA
Chemistry Department, University College, Cork, Ireland
Department
of
Chemistry, Rice University, Houston, Tesas,
USA
Equipe de Recherche
No. 12
du
CNRS, Laboratoire de Chimie,
Ecole Normale Superieure, Paris, France
Institute
of
Organic Chemistry, University of Lausanne,
Lausanne, S\vitzerland
Department of Chemistry, University of Waterloo, Waterloo,
Ontario, Canada
Institute
of
Organic Chemistry, University of Lausanne,
Lausanne, Switzerland
Department of Chemistry, University of Kaiserslautern, D-6750,
Federal Republic of Germany
Fachbereich 14.1 Organische Cheniie, Universitiit des Saarlandes,
D-6600 Saarbrucken, Germany
1
162 Quince Avenue, Sunnyvale, California 94087, USA
Department of Chemistry and Chemical Engineering, University
of Saskatchavan, Saskatoon, Saskatchc\van, Canada
Istituto di Chirnica Fisica, Uni\*ersitB di Perugia,
06100
Periigia,
Italy
Organic Chemistry Department, Institute
of
Chemical Techno-
logy,
5 3 2
10
Pardubice, Czechoslovakia
Department
of
Chemistry, Laurentian University, Sudbury,
Ontario, Canada
Department of Organic Chemistry, University
of
Liverpool,
England
Department of Chemistry, University of
Missouri-Rolla,
Rolla,
Mo. 65301,
USA
V
Foreword
The present volume, ‘The Chemistry of Diazonium and Diazo Groups’ is, on the
whole, organized and presented according to the general lines described in the
‘Preface
to
the Series’, printed
on
the following pages.
Some difficulty arose in the presentation o’wingto the fact that while the two groups
treated, i.e. the diazo group and the diazoniuni group, are closely related and even
occur
irk
equilibrium with each other, their chemical behaviour and characteristics
differ from each other considerably. Moreover, the material which had
to
be covcred
proved to be much more extensive than originally surmised. For these reasons,
some
of
the subjects had
to
be divided into
two
or
more chapters;
for
instance, the
synthetic applications of diazoniuni and diazo groups are treated in two separate
chapters and even
so
each
of
thcse turned
out
to be very large. Similarly, the
syntheses
of
the different
title
compounds are discussed in three separate chapters.
The plan of the present volume
also
included
a
chapter on ‘Biological and
Pharmaceutical Effects’ which, however, failed to materialize. It
is
hoped that this
will appear in one
of
the supplementary volumes
to
the series.
Jerusalem, February 1977
SAUL
PATAI
Vii
The
Chemistry
of Functional
Groups
Preface
to
the
series
The series ‘The Chemistry
of
Functional Groups’ is planned to cover
in
each volume
all
aspects of the chemistry of one
of
the important functional groups in organic
chemistry. The emphasis is laid on the functional group treated and on the effects
which
i t
exerts on the chemical and physical properties, primarily in the immediate
vicinity
of
the group in question, a n d secondarily o n the behaviour
of
the whole
molecule. For instance,
t h e
volume
The
Chemistry
of
[lie Elirer
Liriknge
deals with
reactions in which the C-0-C
group is involved, as well as \vith the effects of the
C-0-C
group o n the reactions
of
nlkyl
o r aryl groups connected t o the ether
oxygen.
It
is the purpose of the volume to give
a
complete coverage of
all
properties
and reactions of ethers
in
as far as these depend
on
the presence of the ether group but
t h e
primary subject matter
is
not the whole molecule,
but
the
C-0-C
functional
group.
A further restriction
in
the treatment of the various functional groups
in
these
voluines is that material included in easily and generally available secondary
or
tertiary sources, such as Chemical Reviews, Quarterly Reviews, Organic Reactions,
various ‘Advances’ and ‘Progress’ series as well
as
textbooks (i.e.
in
books which are
usually found in the chemical librarics of universities and research institutes) should
not, a s
a
rule, be repeated in detail, unless
it
is necessary for the balanced treatment
of the subject. Therefore each of the authors is asked
riot
to give an encyclopaedic
coverage of his subject,
but
to
concentrate o n the most iniportant recent develop-
ments and mainly o n material that has not been adequately covered by reviews o r
other secondary sources by the time of writing of the chapter, and to address himself
to
a
reader who is assumed
to
be at
a
fairly advanced post-graduate level.
With these restrictions,
i t
is realized that n o plan can be dcvised for
a
volume that
would give
a
cortiplcle coverage of the subject with
t i 0
overlap betiyeen chapters,
while at thc same time preserving the readability of the text. T h e Editor set himself
the goal
of
attaining
r~cnsotin6lc
coverage with
modcr.n/c
overlap, with
a
minimum of
cross-references between the chapters of each volume. In this manner, sufficient
freedom is given
to
each author to produce readable qu3si-moiiogrnphic chapters.
The general plan
of
each volume includes the following main scctions:
(a)
A n introductory chapter dealing with
t h e
general and theorctical aspects of
the group.
(b) One o r more chapters dealing
\vith
the formation of the functional group
i n
question, either from groups present in the molecule, o r by introducins the new group
directly o r indircctlj.
(c) Chapters describing the characterization and characteristics of the functional
groups, i.e. a chaptcr dcaling with qualitative
a n d
quantitative nlethods of detcr-
mination including chemical and physical methods, ultraviolet, infrdred, nuclear
IS

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