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Hydrocarbon Chemistry. By George A. Olah and rpd Molnr

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page 98 (Section the reaction of
meso-anhydrides with chiral diphenylboronic esters is presented with no reference to related reactions elsewhere in
the book. On page 113 (Section
the methanolysis of meso-anhydrides
using cinchona alkaloids as chiral bases
is described, but again with no cross-references. On page 200, in the chapter on
asymmetric desymmetrization, the
methanolysis of meso-anhydrides is covered briefly, and only here does one find
a cross-reference to the work in Sections and In the database there
is a record of the desymmetrization of 3substituted glutaric anhydrides by (R)-1phenylethanol, a reaction used by Rosen
and Heathcock in their synthesis of (þ)compactin. The record links the method
to Section in Part I and the chapter on asymmetric desymmetrization in
Part II, even though cinchona alkaloids
are not used. No link is made to Chapter
7, where the reference to the compactin
synthesis is given in Table 7.4. Are you
confused? The database might have
helped allay the confusion by making
the appropriate links.
In summary, Otera's book does a
good job, concisely covering the esterification methodology literature from 1990
to 1999, and that survey will be useful to
synthetic organic chemists. The CDROM is a welcome vehicle for the economical presentation of large amounts
of supplementary material. Indeed, the
experimental procedures that occupy
such a large proportion of Part I might
have been better placed on the CDROM. However, the value of the book
has been compromised to some extent
by omissions. For example, there is no
focussed discussion of macrolactonization (the word does not even appear in
the index), even though a large amount
of effort has been expended on this reaction in the context of macrolide synthesis. Moreover, there are no references
to other monographs and reviews on
esters, esterifications, esters as protecting groups, or biotransformations.
Philip J. Kocienski
School of Chemistry
University of Leeds (Great Britain)
Hydrocarbon Chemistry
By George A. Olah
and rpd Molnr.
John Wiley & Sons,
Hoboken 2003.
871 pp., hardcover
E 165.00.—ISBN
The second edition of this monograph
on hydrocarbon chemistry by George
Olah and 7rp8d Moln8r expands the
earlier 1995 edition by several additional chapters and quite a number of
more recent references up to 2001. The
original idea for this book goes back to
a series of chapters drafted in the late
1970s. Summarizing the chemistry of
hydrocarbons in a single volume is an
almost impossible task, and therefore
the authors had to be selective in their
coverage, which is based on their
expert experience and personal preferences. Thus, the present book is more
of a very well referenced summary of
Olah's lifetime achievements in the
area of hydrocarbon chemistry than a
textbook. The chemistry of hydrocarbons is indeed timely, from both an academic and an industrial viewpoint. The
selective oxidation of methane to methanol, which plays a key role in developing new forms of energy storage, is only
one highly topical theme in this context.
As a consequence, the monograph
covers a very broad range of organic
chemistry that has also appeared in
other places in dedicated chapters, but
the connection to practical and industrial applications makes this work
The 14-chapter book opens with a
general introduction, followed by a
description of how hydrocarbons are
extracted from natural sources. After a
unique and very interesting summary
on “C1-chemistry” (CO, CO2, CH4), several chapters deal with specific transformations of hydrocarbons, beginning
with the industrially important cracking,
reforming, and isomerization processes.
Newer methods are introduced in the
last three chapters.
/ 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
The value of the book lies in the
compact nature of the individual chapters, and in the vast number of references to the original literature, which will
make it easy for the reader to explore
new scientific territory. The index is
quite good, although some of the omissions noticed in the first edition also
remain in the second. The iodination of
alkanes, for example, is mentioned in
the text in several places but does not
appear explicitly in the index. Instead,
under “iodination” it mainly lists additions of iodine compounds to unsaturated systems.
The book is not well-suited as a textbook for students; the mechanistic concepts are not explained in enough
detail to provide sufficient insights for
the uninformed reader. Despite an enormous number of publications in this
area, new theoretical proposals as alternatives to current understanding about
mechanisms seldom appear; the highly
important “two-state reactivity model”
is not even mentioned. Single-electron
transfer as a mechanistic alternative to
direct functionalizations of alkanes is
only touched on, and thus the account
is alarmingly incomplete; also s-bond
metathesis is hardly mentioned. Thermodynamic aspects are often ignored:
how is a student to understand that benzaldehyde can be doubly protonated in
the presence of excess benzene, despite
the fact that proton transfer should be
highly exergonic (Eq. 5.76). Finally,
there are many superficial mistakes in
the structural drawings (in Eq. 6.56, 2c/
3e electron-deficient bonds in cations
are dashed, but represented as solid
lines in diborane; in Scheme 6.10, butadiene is transformed into cyclohexene
without addition of a reactant; in
Eq. 9.54, adamantane is oxidized to
oxaadamantane and not, as expected,
appears on p. 393; in Eq. 9.85, one
finds pentavalent carbon), and in the
various reaction equations (Eqs. 1.1–1.3
are incomplete; charge missing in
Eq. 2.8; hydrogen is formed instead of
water in Eq. 2.23; RH equilibrates with
R+ in Eq. 4.4; “OH” is formed in
Eq. 10.56, and chloride from the generic
“Hlg”). As a result of these errors, the
book cannot be recommended to undergraduate or graduate students.
Angew. Chem. Int. Ed. 2004, 43, 1183 – 1185
The literature coverage is comprehensive and ideal for quickly reviewing
specific topics; some of the errors with
author names and year of citation that
occur in other monographs are repeated
here. Although it is acceptable and commonplace for the authors of monographs to emphasize their pioneer
work in a particular field, some of the
referencing seems overly biased. For
example, it is surprising to see a refer-
Angew. Chem. Int. Ed. 2004, 43, 1183 – 1185
ence to Olah's book Hypercarbon
Chemistry for the “proof” of the existence of CH5+ in solution; looking up
this reference one finds yet another citation that relates to Olah's “unpublished
results” (the ESCA spectrum of this ion
in solution).
The present book is of most value to
industrial chemists, but it is less suited
for academic research and teaching,
because of the many unanswered ques-
tions regarding the mechanisms of
hydrocarbon transformations.
Peter R. Schreiner
Institut f6r Organische Chemie
Universit8t Gießen (Germany)
DOI: 10.1002/anie.200385043
/ 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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chemistry, molnr, georg, hydrocarbonic, olah, rpd
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