Chemosphere No. 12, pp. 999-1006, 1978.Pergamon Press.

Printed in G r e a t Britain

BOOK REVIEW

COMPREHENSIVE ORGANIC CHEMISTRY

The Synthesis and Reactions of Organic Compounds

Chairman of the Editorial Board

SIR DEREK BARTON, FRS
Deputy Chairman
W. DAVID OLLIS, FRS

Reviewed by Lord Todd, PRO,Cambridge:

Volume 1 ( S t e r e o c h e m l s t r y ; Hydrocarbons, Halo Compoundsj Oxygen Compounds; e d i t e d by
J.F. Stodda~,Sheffield )
When I was a young d o c t o t e l research c o r k e r i n o r g a n i c chemistry - and t h a t wee n e a r l y F i f t y
years ego - I j elks a l l ptactlalng otgenlc chemists of the dayj had quite a problem on my
hands. Outs was a large and growing subject with a high Factual content and a tether prim-
i t i v e theoretical base. As • result it was difficult to systemetise or abbreviate by
generallsatlon. To master i t and to use i t requited zeal Familiarity with the vstloua com-
pound types and with reactions and methods. To t h i s end the practising organic chemist
needed not just e simple textbook (of which quite a Few existed) but something a good deal
more comprehensive which he could have on h i s own b o o k s h e l f . He needed a source From which
he could q u i c k l y get b a s i c i n f o r m a t i o n on the b e h a v l o u t and r e a c t i o n s of o r g a n i c compounds
and i n which he could browse end i n c r e a s e not Just h i s Factual knowledge but also h i s
chemlcsl insight. But no single wozk existed to f i l l t h i s need. Of course there were
vest encyclopaedic works l l k e Beilstein end many individual monographs but no single compre-
hensive cork on a reasonable s c a l e . And so we f e l l beck to using two books: ( e ) a general
t e x t ; N l ~ m l l y Karret~ Lehrbuch der Ozoaniachen Chemist and ( b ) • book on methods l i k e Houben-
Weyl, Methadon der 0rganiechen Chemie o r , i f we were hezd up; the s h o r t e r end cheaper Meyer,
Analyse und K o n l t i t u t i o n s a c m i t t l u n 9 0¢ganische¢ Vetbindungen° During the F i f t y years since
then the situation has not improved. Certainly we have extensive and detailed works l i k e
Rodd's Chemistry of Carbon Compounds which i s an Invaluable source or Factual informer/on,
but Is so large that i t can be regarded as eeemntlally a llbrmry work of reference rather
then one which individuals keep on t h e i r own shelves end reed regularly. This i s perhaps
the inevitable consequence of the staggering growth or organic chemistry during the past
half-century; t h i s growth no doubt accounts in part For the enormousexpansion of Houban-
~yl. The 3¢d Edition of thet work, which ran to four submtmntlal volumes, although
immensely valuable was cloee to the l i m i t in size for the individual reader; but the new 4th
Edition i s 8o enormous that i t i s quite beyond the pocket of the individual (and perheps even
of some l i b r a z i e s ) end has l o s t some o? i t s original character. Both of these r e f e r e n c e
~zka incidentally have a major d e f e c t i n h e r e n t i n t h e i r slow r a t e of p u b l i c a t i o n : earlier
volumes oF each ace not l n f c e q u a n t l y o u t - o F - d a t e beFoce some l a t e r ones appear.

999
1000 Book Review No. 12

There remains t h e r e ? a t e 8 gap i n the l i t e r a t u r e o f o r g a n i c chemistry which I s even mote

setloua today than i t was in the past, Fat thl8 reason one must applaud the task which the
editors and publishers of Comprahenalve Or~onlc Chemistry have set themselves in t t y l n g to
F i l l t h i s gap and by undertaking to publish the s n t l t e work on s mld-lg?7 cove=age dsadllns
during the f i r s t 3 months of next year. I f t h l s Is achlevad i t w i l l be 8 spectacular
technical echlevement. The intention Is to issue the whole work in 6 volumes of around
1200 pages each and t h i s a r t i c l e le specifically concerned w i t h Volume 1, My comments on
the work as a whole r e s t t h e r e f o r e on the assumption t h a t Volume 1 t8 t y p i c a l of them a l l ~
?tom i t s layoutp its list of c o n t e n t s j and my perusal o f the i n d i v i d u a l chapters t h i s would
8oem s not unreasonable s e s u m p t t o n t o m a k e .

I confess t h a t I have boon much impressed by Volume 1~ l s r g o l y ~ o f courss~ because i t moots

my c r i t e r i a f o r 8 personal re?stance t e x t f o r the p r a c t i s i n g o r g a n i c c h m l e t , The coverage
i s on o r t h o d o x l i n e s and comprises s l t p h a t i c and 8 1 1 c y c l i c hydrocarbonej arana8~ h a l o -
compounds9 alcohols9 phenolaj c a r b o n y l compounds and e t h e r s , It c o n t a i n s the oaeenti81
f a c t u a l matter on i n d i v i d u a l groups o f compounds but employs what I would c a l l the Houbon-
Weyl approach to methods and r e a c t i o n s modocnieed on the b a s i s of mechanistic ideas and i t
g i v e s copious and~ on the wholop well-chosen r e f e r e n c e s t o mote d e t a i l e d sources of
information, Volume 1 t n c l u d e s j i n a d d i t i o n t o chapters on i n d i v i d u a l compound groups s
o t h e r s on t h e o r e t i c a l t o p i c s such as e t a t o o c h e m l s t t y end a t o m a t i c i t y which ore d e a l t w i t h i n
a t h o r o u g h l y u p - t o - d o t s manner, On r i r a t approaching i t I felt the opening chapter on
e t e r o o c h e m i e t r y woe c u r i o u s l y locatod~ but on f u r t h e r r e f l e c t i o n I t h i n k t h a t t h i s may be
rather unfair, This book I s i n no sense on i n t r o d u c t o r y t e x t on o r g a n i c chemistry f o r
undergraduates and to give a comptohonelvo treatment of modern ststoochemlatry 8a a kind of
introduction may wall be desirable. One criticism which I would make i s that the balance 18
not in my opinion always perfect; for instance I Find i t hard to belleva that quinona8
warrant no mote than 12 pages (and these mainly on bonzoquinone8) whereas 40 pages ate
devoted t o annulonss, or coutaap t h e r e ate always d i f f e r e n c e s o f o p i n i o n on the r e l a t i v e
importance o f i n d i v i d u a l t o p i c s Just sa t h e r e ate d i f f e r e n c e s i n s t y l e o? p r e s e n t a t i o n by
individual authors9 but although t h e r e Is9 hero and t h o t e j a l i t t l e unevenness i n a t y l e ~ the
e d i t o r s have done such an e x c e l l e n t Job i n c o n t r o l l i n g general t r e a t m e n t of t o p i c s t h a t any
unevenness i s not o b t r u s i v e , Somao t h e r minor c r i t i c i s m s could bs made but they would not
affect my vlaw that this ptomlaee to be a roe1 conttlbution to the l i t e r a t u r e of organic
chemistry. I t i s not in competitlon with the encyclopaedic works of reference which we have
but 18 s comprehensive f i r s t source to which the chemist can turn ?at information and in
which he can brown for inspiration. I f the other f i v e volumes adequately match the f i r s t
then Comp¢ehonsive Organic Chemistry will fill 8 long-felt need and should be 8 success,

Reviewed by G. Ourisson. Strasbourg:

Volume 2 ( N i t r o g e n Compoundlj C a i b o x y l l c Acid8~ Phosphorus Compounds; e d i t e d by
I O. Suthedand. Liverpo~
The peasant volume i s p r o b a b l y t y p i c a l of the complete a e r i e s , I t I s ' m e d i u m - a i z s d ' j has a
vary wide covetagsj ¢ l l l e e heavily on existing tsvlewa and books9 and Is d a ? I n l t l l y up-to-
date.

I t s medium elze i s in l i n e with the B t l t l a h t t a d l t i o n of Rodd'8 'Chemistry of Carbon

No. 12 Book Review 1001

Compounds ~, and runs o p p o s i t e t o the German i d e a l o f t h e e x h a u s t i v e Hsndbuch, es w e l l as t o

t h e American one o f the s p s c i s l i s e d monograph. This i n t e r m e d i a t e c h a r a c t e r makes i t
certainly e a s i e r f o r t h e r e a d e r t o scan f o r t h e e s s e n t i a l p o i n t s i n a domain new t o him, a t
a l e v e l deeper than t h a t medo a c c e s s i b l e by t e x t b o o k s , end w i t h t h e p r o v i s i o n o f key r e f e r -
ences to the primary l i t e r a t u r e , end to epsciellsod reviews. In most chapters, the b i b l i o -
graphy c o n t a i n s t h e e s s e n t i a l r e c e n t books, mentions e x t e n s i v e l y Chemical Reviews o r Organic
R e a c t i o n s , Houben-Wsyl o r P a t a i # i n b r i e f does n o t m a k e - b e l i e v e t h a t t h e a u t h o r has reed e l l
the p r i m a r y r e f e r e n c e s q u o t e d , and o n l y p r i m a r y l i t e r a t u r e . This i s o f course a l l t o the
advantage of the reader, who w i l l certainly went to begin his reading by such reviews. Let
us n o t e s t t h i s stage t h a t t h e l a t e s t t o ? s t a n c e s mentioned are from 1976-1977, and t h a t i n
most chapters, the patent l i t e r a t u r e i s p r e c t l c a l l y ignored. (In thl8 respect recourse to
Houben-Weyl would provide often e completely d i f f e r e n t p i c t u r e . )
The coverage i s vmry wide. In t h i s volume o f some 1300 pages, e i g h t e e n c h a p t e r s d e s c r i b e
classical f u n c t i o n s (amines o f d i v e r s e types# n i t r l l s s , eaters# e t c . ) , as well as more
s p e c i a l ones ( e . g . n t t r o n e s , nttroxidee, phosphazsnes...). In each case, a c l e e m t c a l p l a n
is followed: p r e p a r a t i o n s end r e a c t i o n s e r e covered i n turn~ w i t h u s u a l l y o n l y • wary b r i e f
mention o f t h e p h y s i c a l p r o p e r t i e s and o f s t r u c t u r a l aspects. In general# mechanisms ere
h a r d l y d i s c u s s e d , except when t h e y have a d i r e c t b e a r i n g on the p r e p a r a t i v e a s p e c t s .
The v a r i o u s c h a p t e r s a r e t r e a t e d i n a s i m i l a r manner, but n o t a t t h e same l e v e l or d e t a i l .
For i n s t a n c e , t h e c h a p t e r on l m i n e e , n i t r o n e s ~ n t t t l l e s end imocyenldee i s e x c e p t i o n a l l y
thorough ( n e a r l y 200 pages, 650 r e f e r e n c e s ) # whereas a r o m a t i c amines, t o which c e r t a i n l y
much mote work has been devoted# ere covered i n 50 pages, w i t h some 200 r e f e r e n c e s . In f a c t #
I b e l i e v e t h i s i s p r o b a b l y once again fevourablm f o r the reader# who g e t s most o f what h i
needs most: h e l p w i t h t h e l e s s a c c e s s i b l e i n f o r m a t i o n .
It Is extremely difficult to gauge such a l a r g e book by scanning i t o r by r e a d i n g p a r t s o f
it; i t i s also certainly not meant to be read through. An impression can however be
gained easily in the few hours I have spent probing, reading, comparing. I t Is d e f i n i t e l y
very revourable. I am convinced t h a t t h e emphasis i s r i g h t ; t h a t t h e book, end c e r t a i n l y
t h e seriee~ w i l l f i n d d a i l y use i n most o r g a n i c chemical l a b o r a t o r i e s # r o t q u i t s a l o n g t i m e .
0r c o u r s e , i t will be most u s e f u l o n l y t o those who have access t o e w e l l - s t o c k e d l i b r a r y ,
but i t must be p o i n t e d o u t t h a t , even from t h a t p o i n t o f view# t h e r e a d e r has been f a v o u r e d ;
a t l e a s t t h e Anglo-Saxon reader9 ee t h e b u l k o f the ro~etencss are t o American end B r i t i s h
articles, with only occasional Intrusion o f German ( f e w ) , 3apaness ( v e r y f e w ) , Swiss,
Russian o r French papers ( r a r e ) .

Reviewed byG. Stork, New York:

Volume 3 ( S u l p h u t # Selenium s S i l i c o n # Boron# O r g e n o m e t a l l t c Compounds; e d i t e d by
D. Neville Jones, Sheffield)
This volume s t a r t s with the organic chemistry of sulfur# from t h t o l m t o t h t o c e r b o n y l coB-
pounds# v i a s u l f i n y l a m i n e s and t h i o s u l f o n a t e s # which i t c o v e r s i n some 480 pages w i t h almost
2pO00 r e f e r e n c e s . This I s f o l l o ~ d by organoeelenium and t e l l u r i u m compounds (46 pages,
2?9 r e f e r e n c e s ) , o r g a n i c compounds o f s i l i c o n (145 pages, 633 r e f e r e n c e s ) , and o f boron (251
pages, 842 r e f e r e n c e s ) . We then encounter o r g a n o m e t a l l i c compounds o f groups I , II, III and
IV, and o f antimony and bismuth (175 pages# ??? r e f e r e n c e s ) . The volume c l o s e s w i t h
1002 Book Revieu NO. 12

o r g a n i c compounds of the t r a n s i t i o n metals (196 pages 179 r e f e r e n c e s ) . This i s s b r e a t h -

taking accomplishment fiat many reasons.

The sixteen w r i t e r s or Volume 3 are not only possessed or what appears to be an encyclopasdlc
knowledge of t h e i r subject. They arej without exception, deeply involved In rssmarch i n
the Field they cover and are, Indead~ immediately reoognlzad as among the Foremost contrib-
utors to i t s recent developments. That such s galaxy or authors could be assembled, that
i t could bring such a project to F r u i t i o n on schsdule~ that i t could maintain soma unity or
preaentatlon and a l a r g e l y successful concern For relevance to synthetic organic chemists, i s
an extraordinary achievement. The Chairman of the E d l t o r l a l Boerdp Professor D.H.R.Bartonj
his Daputy~ Professor W.D. Ollls~ as u a l l as the Editor of t h l s p a r t i c u l a r volumaj Dr.D.N.
3ones~ have our admiration and deserve our thanks.

3udging by t h i s volume~ uhlch I take to be representative of the uhols uork~ I t i s clear that
every serious chemistry l i b r a r y u l l l have to acquire t h i s sat.

This being aeld~ I u i l l now comment more s p e c i f i c a l l y on the material in Volume 3 i f only to
show that my recommendation i s based on actual reading or t h i s volume. I uill s t a r t with
some minor c r i t i c i s m . The book Is completely orlsnted touard leading the practising chemist
to racsnt~ o p e r a t i o n a l l y ussFul~ l i t e r a t u r e references on e p a r t i c u l a r rsactlon. In t h i s I t
hem succeedsdj and t h i s i s obviously a major strength, but s c o r o l l a r y i s that t h l s i s not a
book uhlch can be consulted to get sense or the h i s t o r y of i n t e l l e c t u a l background of a
method. To give but three exomples~ the rearrangement of p e n i c i l l i n sulroxlda to caphalos-
porlns i s discussed ulthout mention of the seminal uork of Rorln and the L i l l y Laboratories;
the a l k y l a t l o n or carbanlons to thlolsulronates Is discussed u l t h no references to Smiles;
the contribution or Tsujl in the usa of palladium complexes to Form carbon-carbon bonds i s
mentioned, but there i s no suggestion or i t s pioneering nature. Thls i s not so much a
c r i t i c i s m as a rsmlnder to the users of the book.

The book i s not especially concerned u l t h mechanism and i t s usefulness Is~ therefore, not
r e a l l y affected by the (very feu) questionable ststemsnts one i n e v i t a b l y encounters, such as
comments on the addition of benzoylsulrena (p.41g)~ on the reason For the Foreatlon or
a l l y l l c alcohols From seZanoxldss (compare p.494 u l t h p.501), on uhat Is~ perhaps unfortun-
ately= termed l~3-addltlons to carbonyl compounds (p.g81)= on the nature of Zn anolete=
(p.992). Rialsadlnl statements ere~ as one uould expect, extremely rers~ one such concerning
the suggested g a n a r e l l t y of the addition of Grlgnard rsa9ents to Imlnes.

T h e r e e r a some s u r p r i s i n g omtesions= inter slis~ no e x p l i c i t m e n t i o n oF t h e o p a n t n g or

epoxldes u l t h athynyl alanes~ the reductlon or n l t r l l s s to aldehydes u l t h dilsobutyalumlnum
hydrlde~ the use or ~-heterosubstituted l i t h i u m end magnaslum reagents~ the conjugate
reduction oF0~-unsaturatad carbonyl compounds u l t h t l n hydrides, o x i d a t i v e and p r o t l c
dmstmnnylatlon. Someq u a l i t a t i v e me©hanlatlc statements uouZd somatlmea have helped, e . g . ,
Formation of a z l r l d l n e s From oxlmes (p.gT8). On the other hand, the rather esoteric and
anmeuhat l i m i t e d opaning o f epoxides u t t h HCo(CO)4 l a mentioned t u t c e u l t h equations (p.1149
and 1236).

The e d i t o r s have o b v i o u s l y s t r u g g l e d t o minimize diFFerences i n s t y l e and p r e s e n t a t i o n . Even

then~ tuo chapters ( o r g a n i c compounds oF group I and I I metmla) do not q u i t e coem up t o the
NO. 12 Book Review 1003

standards of the others. They w i l l p r o b a b l y n o t add much t o t h e fund of knowledge o f the

average s y n t h e t i c chemist. T h i s i s perhaps u n d e r s t a n d a b l e s i n c e these areas are covered
quite extensively in widely available monographs. On the other hand, the chapter by lan
fleming on orgsnosilicon chemistry is superb in every respect. I recommend its reading not
only to the aficionados, but to anyone contemplating writing a book or a chapter. This is
not meant to s l i g h t other Chapters or t h e i r w r i t e r s : the chapter by O. St.C.Blsck, 3.3.Swan
and W.R. 3ackson represents a signal accomplishment i n orgsnising enormous amounts of
m a t e r i a l , as do the chapters by A. P e l t e r and K. Smith on boron compounds, to mention only
tuo among several.

In conclusion, with the very few exceptions noted above, every important reac~bn ( t h a t I
knew about) i s covered here: from t h i o Claissn rearrangement to the use of Burgess' s a l t f o r
dehydration, and o f methylene t h i o s u l f o x i d e s as csrbanion equivalents. Many more t r a n s -
formations that one would l i k e to be f a m i l i a r with ere now presented in convenient and
completely up-to-date fashion.

tComprehensive Organic Chemistry' w i l l be an a l l but e s s e n t i a l companion in synthetic

explorations.

Reviewed by R ULemieux, FRS, Edmon~n:

Volume 4 ( H e t e r o c y c l t c Compounds; e d i t e d by P G Sammes, London )
This fine contribution well surveys the exceedingly complex and ramified field of
hetsrocyclic chemistry while remaining pleasantly readable. The focus is on the unsaturated
heterocyclic ring systems with concentration on synthesis, chemical properties, reactions and
mechanisms of reaction. These fundamental aspects are discussed and interpreted in
uniformly competent, modern and critical modes. Some insights are provided to the great
significance of heterocyclic chemistry to such areas as chemotherapy, photographyp agri-
culture and dyestuffs. The quality of presentation and documentation in these latter
regards is highly variable. Such s shortcoming was inevitable. The work is alrzsdy of
heroic proportions.

The volume i s d i v i d e d i n t o five parts: t h e azino8 (? s e c t i o n s , 272 p a g e s ) , t h e a z o l e s (5

sections, 329 p a g e s ) , oxygen systems (5 s e c t i o n s , 179 p a g e s ) , s u l p h u r and o t h e r heteroatom
systems (3 s e c t i o n s , 168 p a g e s ) , and mixed h e t s r o a t o m systems (4 s e c t i o n s , 25? p a g e s ) . All
s e c t i o n s are i n t r o d u c e d w i t h s t a b l e of c o n t e n t s and t h e r e b y u s e f u l l y self-indexed. The
work by 22 a u t h o r s and e d i t e d by P.G. Sammss c o n t a i n s near 4000 r e f e r e n c e s t o , or t o p a r t s o ~
t h e near 500 r e v i e w a r t i c l e s . The v a s t l i t e r a t u r e which has appeared i n the more r e c e n t
y e a r s appears w e l l c o v e r e d . The t e x t s are a s s i s t e d by w e l l chosen end p r e s e n t e d f o r m u l a e ,
diagrams and t a b l e s .

The volume will serve as a sound base and guide to a vast field of chemistry which is
harvested by virtually all chemists. It will undoubtedly find extensive use in both
industrial and academic libraries. Consultants and research chemists should consider it
for office usage - the r e t r i e v a l i n a c o h e r e n t f a s h i o n o f a wide range o f i m p o r t a n t f a c t u a l
knowledge has been made reliably convenient.
t004 Book Review No. 12

RevlewedbyW.S. Johnson, Stanford:

Volume 5 ( B i o l o g i c a l Compounds; e d i t e d by E. Ha#dam,Sheffieid)

As s t a t e d i n t h e I n t r o d u c t i o n j t h e c o n t e n t s o f t h i s volume hove 'bean aemombled n o t so Much

t o be f u l l y comprehensive as t o be comprehensiblep t o r e f l e c t what a t e Judged t o be the t r u l y
important facets of the present state of biological organic chemistry.' I am pleased t o say
t h a t these aims have boon achieved a d m i r a b l y . To a s y n t h e t i c o r g a n i c chemist t h e c h a p t e r s
are n o t o n l y comprehensible but I n t e r e s t i n g end h i g h l y i n f o r m a t i v e . Am i s seen by the
comments below s which i n c l u d e some o f those (paraphrased by me) o r a number o f my c o l l e a g u e s
who k i n d l y examined s e l e c t e d s e c t i o n s f a l X l n g w i t h i n t h e i r own s p e c i a l t y s t h e book on t h e
whole does indeed c o v e t t h e a f o r e m e n t i o n e d i m p o r t a n t f a c e t s i n • t r u l y s c h o l a r l y manner. The
e x c e p t i o n s noted r e p r e s e n t e t e t h e r t r i v i a l p a r t o r t h e whole.

P e r t 21 Biological Chemistry: An I n t r o d u c t i o n by Et Haslem.

This i s an e l o q u e n t s t a t e m e n t t h a t h i t s the center of the bullseye. I could have wished
o n l y t h a t t h e term ' b i o m i m e t i c ' had been adopted i n p l a c e o f the o l d e r mote awkward
expressions ' b i o g e n e t i c l i k e ' or 'biogenetic type' - e t r i v i a l matter indeed.

P e r t 22 N u c l e i c Acids: by G~Rt B l a c k b u r n | N u c l e o s i d e s m by RtT , Walker: Nug199ttdes and

R e l a t e d Organic Phoephates~ by D~WT H u t c h i n s o n | N u c l e i c Acids: S t r u c t u r e end F u n c t i o n . by
G~M~ B l a c k b u r n . Reviewed w i t h G.W. Daub. Besides p r o v i d i n g the o r g a n i c chemist w i t h 8
good exposure t o fundamentals o r t h e f i e l d s new developments and some o r the more
s o p h i s t i c a t e d a8pecta a t e , t e a t e d t o promote u n d e r s t a n d i n g a t 8 h i g h e r l e v e l . The coverage
i n c l u d e s work up t h r o u g h 1977.

P a r t 23 Proteins: Amino-acids and P e p t i d e e : I n t r o d u c t i o n I by E~ Haalem| Amlng-eclds Found

i n P r o t e i n e ~ by P~RT Hardy; P e p t l d e e and t h e P r i m a r y S t r u c t u r e o f P r o t e i n 8 t by D.T~ E l l o t e ;
N a t u r a l l y O c c u r r i n g Low M o l e c u l a r Weight P e p t i d e e I by W t B y c r o r t | ~-Lactem A n t i b i o t i c s m by
Gt Lows| P e p t i d e S y n t h e s i s , by RtC ~ 5 h e p p l t d | C~n?ormetions o f P o l y c e o t i d e e ! ~y GtCt
Barrett| and P a r t 24 P r o t e i n s : Enzyme C a t a l y s i s and F ~ n c t l o n e 1 P r o t e i n s : Enzvle C a t a l y s i s ,
by AT 3~ K i t b y ~ Chemistry o f Other P r o t e i n s m by DtT ~ Elms,e| CoanzYmes. by H.C.5. Wood|
Witemin B12 ~ by B.T. G o l d i n q . Reviewed w i t h D.H. Rich. E n t i r e monographs have been
devoted t o each o f t h e major t o p i c s coveted i n these s e c t i o n s ; hence i t has been p o s s i b l e t o
g i v e o n l y an a b b r e v i a t e d t r e a t m e n t . N e v e r t h e l e s s t h e e x p o s i t i o n i s e m i n e n t l y s u i t a b l e ?o¢
i n t r o d u c i n g t h e s u b j e c t m a t t e r t o chmmiets l a c k i n g b i o c h e m i c a l backgrounds. A few Minor
criticisms are n o t e d . The c h e m i s t r y o f b l e o m y c i n c o u l d w e l l have been covered a l i t t l e more
t h o r o u g h l y since t h i s a n t i t u m o r compound i s an i m p o r t a n t t h e r a p e u t i c a g e n t . A rather
uncritical v i e w or t h e s t a t e - o f - t h e - a r t of p e p t i d e s y n t h e s i s i s p r o j e c t e d s i n p a r t i c u l a r some
delineation of difficulties encountered s w i t h s i d e r e a c t i o n s ( i n c l u d i n g ¢ a r a t e n c e s ) ~ would
have boon welcome. A number o f i m p o r t a n t l i t e r a t u r e citations hove boon o m i t t e d s e . g . i n
c o n n e c t i o n w i t h t h e r e a c t i o n o f 89->90 ( e q u a t i o n 9) on page 345.

P ~ r t 25 L~Bi# C h p i m t r y end B l o ~ h e m i e t r y : F a t t y A c i d s . by F.D. Gunetonel L1pidtm by F~D.

G~nstone; M~lbtmnee and L l p o p r o t e i n s , by P~F ! Knowlee. Reviewed w i t h H.R.RcConnell.
This is e f i r s t - c l a s s treatment of the subject. Even from the p o i n t o f v i e w o f the b i o -
chemist o¢ b i o p h y s i c i s t its weaknesses a t e p ¢ l n c i p a l l y matters of omission. I t i s pechapa
worth n o t i n g t h a t these l a t t e r scientists ~uld regard cholesterol ( e l w e l l as n a t u r a l
No. 12 Book Review 1005

d e t v l e t l v e s of f a t t y acids) as a l i p i d . One also might question the implication that the

maJotlty of proteins occutrlng i n membranes are enzymes. Be t h a t as i t meyj t h i s i s a
splsadld exposition of the subject f a t a chemical sudlence.

P a r t 26 Carbohydrate Chemistry: Ronoeeccheride Chemiettya by L~ Houoh sad A.C. Richardson;

Olioos~ha¢lde C h l m i a t r y j by L, Hough sad A~Cm Rlchecdeon| P o l y s s c c h e r i d e a . by 3.F.Kennedy
sac CtA + White~ P q l y e a c c h a r i d e s : C g n f g t m a t t o n a l P r o c e t t i l e i n 5 o l u t i o n I by DgA~ RIOSo
Reviewed w i t h G.A. Croaby. In a d d i t i o n t o a c l e a t and concise t r e a t m e n t o f monosaccharida
chemlstry~ an i n t e r e s t i n g section on sugars containing heteroatoms i s Included9 i . e . emlno-
and halosugars. A timely addition would have been some i l l u s t r a t i o n of the usa of sugars
as c h l r a l synthons and templates f o r asymmattlc synthesis of natural products. The f o u r -
page section on ollgosacchsrlde chemistry i s probably too b r i e f sa i t barely touches on the
subject. The polyaaccharlde section i s especially good and up-to-date (48~ of the
refarancas~ 1970). Rote a t t e n t i o n c o u l d have boon g i v e n t o r e a c t i o n s o f p o l y s a c c h a t i d a s .
The section on conformation seems to be very good and up-to-data (95~ of the r a f e r e n c e s ~
1970).
P a r t 27 S y n t h e s i s o f Otganlc Racromoleculam and t h a l t Uses i n Organlc Chemlstty I by P.HodQa.
Reviewed w i t h G.A. Crosby. This s e c t i o n i s w e l l - w r i t t a n p easy t o comprahend~ a c c u r a t e and
interesting° However, t h e coverage i s t o o b r i e f (30 pages) and some i m p o r t a n t t o p i c s are
almost i g n o z a d . Fat example, t h e t r e a t m e n t o f t h e s y n t h e s i s end p r o p e r t i e s o f macromole-
c u l a e c o v e r s o n l y 19 pages as compared w i t h 40 i n Roberts and C a a e r i o ' s Basic P r i n c i p l e s or
Organlc Chemistry (2nd ed.). In the section on sppllcatlons9 the treatment of cross-llnked
polymers i s excsllentp but there are some other important subjects which could have been
covered, including reactions of soluble polymers end selected i n d u s t r i a l applications.

Pkrt 28 S i c - O r g a n i c Chemistry: B i o s y n t h e s i s ! by R. Thomas| P h o t o s y n t h e s i s m N i t r o g e n F i x a t i o n

and I n t e r m e d i a r y R e t a b o l i s m I by E. Haslam. P a r t 29 B i o s y n t h e t i c Pathways from A c e t a t e :
Polyketldo Biosynthesis! by 3.D. 8u'lock; Tarpenold Bloeynthealst by 3~RT Hanson| Carotenoid
Biosyntheele sad Vitamin Am by G~ B r l t t o n . Part 30 Biosynthesis - A General Survey:
Alkaloid Biosyntheslsm by R~B. Herbert| Potphytlnm ChlorophyllI and Cotrln Bloaynthaelsm by
R+ A k h t s r end P~M~ 3ordan| 5 h i k l a i c Acid ~ a t a b o l i t e s I by E~ Haelam. Reviewed w i t h R . 3 . P a r r y .
Aside from a s l i g h t organizational problem~ i . a ° all o f Pact 29 seemingly belongs unde¢ the
heading o f P a r t 30, these c h a p t e r s are e x t r e m e l y w a l l - w r i t t e n . The m a t e r i a l i s q u i t e u p - t o -
d a t e t h r o u g h 1975, and t h e i m p o r t a n t aspects o f the f i e l d have been covecad i n • s c h o l a r l y
manner. In seeking p e r f e c t i o n one can f i n d o n l y minor areas f o r improvement, i . e . Chart 2
on page 919 and Chart 4 on page 925, p a r t i c u l a r l y the fotmat~ a t e d i f f i c u l t to interpret; In
Schema 7, p. 1053j i t ta Incorrectly i m p l i e d t h a t the mechanism o r r e d u c t i o n o f t h e p y t i d i n e
ring of n i c o t i n i c acid hal been establlahed; the representation of the sdduct or thlmmlna
pyrophosphate and ~ - k e t o g l u t a r i c a c i d ( i n Schemes 16j 33 and 34, pp. 1184, 1200 and 1201) as
a naked c a r b o n i o n ( h a v i n g a c i d i c hydrogens) l e n o t r a c y s a t t s f a c t o c y .

In c o n c l u s i o n , Haslam and h i s c o l l a b o r a t i n g c o a u t h o r s are t o be c o n g r a t u l a t e d f a t p r o d u c i n g

such a m a g n i f i c e n t segment o f t h e 8 a r t o n - O l l i s magnum opus which indeed t e p t e s s a t e a major
contribution to scholars of organic chemistry.
1006 Book Review NO. 12

Reviewed by J. E. Baldwin, FRS Oxford:

Uolume 6 ( A u t h o r , Formulaj Subject 9 Reagent, Reaction Indexes; e d i t e d by C.J. Drayton, Oxford )

This review will be published in s subsequent issue.

Comprehensive Organic Chemistry is published in six volumes (approximately 8000 pages) by

Pergamon Press, Oxford and New York. Price US~1250 (£625).