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Book Review The Chemistry of Sulphenic Acids and their Derivatives. Edited by S. Patai

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Chem. 28 (1989) 1985; b) G. Lopez, G. Garcia, J. Ruiz, G. Sanchez, J.
Garcia, C. Vicente, 1 Chem. SOC.Chem. Commun. 1989,1045;c) G. Lopez,
J. Ruiz, G. Garcia, C. Vicente, J. M. Marti, M. D. Santana, 1 Organomer.
Chem. 393 (1990)C53.
[4] H. E. Bryndza, W.Tam, Chem. Rev. 88 (1988)1163.
[5] Unpublished X-ray diffraction data have established the binuclear nature
of [(C6F,),Ni(~-OH),Ni(C6F~)~]ze,
with an average Ni-0 bond length of
1.91 A.
[6] [NBu,),[((C,F,),Ni(~-OH)} ,] (0.150 g, 0.115 mmol), was added to a solution of malononitrile (0.759 g, 11.5 mmol) in benzene (50mL) and the
mixture was refluxed for 2 h. The benzene was evaporated under vacuum
and the resulting sticky material was treated with ethanol and vigorously
stirred to give a beige solid, which was isolated (55% yield) and identified
(Trimer I). Coras 4,6-diamino-2-cyanomethyl-3,5-pyridinedicarbonitrile
rect C,H,Nelementalanalysis. M.p. 330°C. M S : m / z 198(Me, 100%); IR
(Nujol): Q [cm-']=3400-3200, 1600, 1560, 1500; VIS-UV (in MeOH):
A,,, [nm]=313, 245 (sh), 237. 'H-NMR (80 MHz, [D,]acetone, TMS):
6=4.15 ( s , 2H), 7.45 (s, 2H), 7.65 ( s , 2H).
[7] H.Inoue, K. Hara, J. Osugi, Rev. Phys. Chem. Jpn. 46 (1976)64.
[8] A . J. Fatiadi, Synthesis 1978, 165.
191 W.J. Geary, Coord. Chem. Rev. 7 (1971)81.
[lo] It is interesting to note that in platinum complexes contaming the [NCCHCOOMe)e ligand, the presence of a sharp, strong band at 2200 cm- '
was attributed to a Pt-CH(CN)COOMe) linkage, whereas a broad, strong
band at 2150-2120cm-' was attributed to the N-bonded structure PtN=C=CHCOOMe: D. P. Arnold, M. A. Bennett, J, Organomef Chem.
199, (1980)119.
[I11 X-ray structure analysis of 1: Philips PW 1100 diffractometer, graphite
monochromator, Cu,, radiation; triclinic, space group Pi,a= 11.614(1),
b=13.836(1), c=11.351(1)A; %=109.90(1), ~=lOO.SS(l), y =
93.66(1)"; Z= 1; psalrd=
1.4301 gem-? 5684 reflections were measured
and the structure was refined, using 2600 data for which I 3.0u(l), to
converge with R=0.087 und R,=0.078. Anisotropic thermal parameters
were assigned to non-hydrogen atoms, while the H atoms were included as
fixed contributors to the structure factors. Further details of the crystal
structure investigation are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft fur wissenschaftlich-technischeInformation mbH, W-7514 Eggenstein-Leopoldshafen 2 (FRG), on quoting
the depository number CSD-55150,the names of the authors. and the
journal citation.
[I21 M. M. Brezinski, J. Schneider, L. J. Radonovich, K. J. Klabunde, Inorg.
Chem. 28 (1989)2414.
The Chemistry of Sulphenic Acids and their Derivatives. Edited by S . Patai. Wiley, Chichester 1990. xvi, 819 pp., hardcover, E 190.00.-ISBN 0-471-92373-9
This volume of the Patai series sets out to provide a comprehensive account of the current state of knowledge concerning the chemistry of sulfenic acids and their derivatives.
It can be said at the outset that this aim has, by and large,
been fulfilled.
As the negative aspects of the book are in the minority,
these will be mentioned first. Local patriotism in the choice
of literature references can be justified in a publication intended for a local readership, even though it is of little value;
however, an internationally orientated work should not concentrate almost exclusively on citations originating from the
United Kingdom and the USA, as one finds in Chapters 1,
2 and 9. Nor should about 50% of the references be to the
author's own publications, as is the case in Chapters 13 and
15. While on the subject of literature citations, it is remarkable that the name H . Bohme (Marburg) is only once cited (in
0 VCH Verlagsgesellsehaf~ mbH, W-6940 Weinheim, 1991
Chapter lo), even though he could hardly be regarded as a
minor contributor in the field of sulfenic acid derivatives!
The only possible excuse for this is that many of the chapters
contain references to earlier review articles. A further criticism is that there are few references to recent publications;
for example, of the 70 references in Chapter 18 only eight are
to publications after 1980.
In a monograph on sulfenic acids and their derivatives one
can criticize the omission of the chemistry of sulfenyl carboxylates (mixed anhydrides of sulfenic and carboxylic
acids); the only mentions of these are in the well-balanced
contribution by Horspool (Chapter 11, pp. 539- 540) in connection with their photochemistry, and in Table 15 (Chapter
10, p. 449) without further details. It seems strange that
D.R.Hogg (Chapter 9) has not mentioned this class of compounds, which he has himself previously studied (see Ref. [7]
in K. Schank et al., J. Org. Chem. 48 (1983) 4580). It would
also have been desirable to mention here the mixed anhydrides of sulfenic and sulfonic acids (K. Schank, F. Werner,
Phosphorus Sulfur 8 (1980) 335). Another puzzling question
is that of the meaning of Table 1 (Chapter 1, p. 12) which lists
bond lengths; this reviewer was unable, on the basis of the
element symbols given, to relate these data to the formulas
above and the compound classes to the left of them. Also the
tables on pages 550-563 are only likely to be understood by
readers familiar with the subject.
There are some excellent contributions that deserve a special mention, namely those by A . R . Bassindale and I . Iley
(Chapter 4), M . Mikolajczyk et al. (Chapters 5 and 6), S .
Braverman (Chapter 8 ) , G . Capozzi, G . Modena and L.
Pasquato (Chapter lo), W M . Horspool (Chapter Il), M .
Zielinski and M . Kanska (Chapter 14), H . C . J. Ottenheijm et
al. (Chapter 16 ) and P. K . Claus (Chapter 17); these chapters
are in themselves enough to make the book worth buying.
Another good feature is the unusually small number of printingerrors (examples of these few are Equation 17 on page 97,
0570-0833/91j0606-0718$3.50+ ,2510
Angew. Chem. I n t . Ed. Engi. 30 (1991) No. 6
where four methyl groups have unexpectedly become five,
and formula 117 on page 455, which has a pentavalent carbon).
Lastly we come to the price. Books can be classified as
cheap (rarely found), expensive (very common) or good value for the price. The reviewer places this one in the third
category. It should be in every chemical library, and can be
recommended to all chemists and biochemists other than
those who associate sulfur compounds only with awful
smells and keep well away from them.
The Chemistry of Sulphinic Acids, Esters and their Derivatives. Edited by S. Putai. Wiley, Chichester 1990. xvi,
728 pp., hardcover, f 165.00.--ISBN 0-471-91918-7
In this further volume of the Putai series the aim was to
give a comprehensive treatment, in 23 chapters, of sulfinic
acids and their derivatives. It can be said at the outset that
the conception of this volume is not nearly so successful as
that of the volume on sulfenic acids. What should one expect
of a work whose objective is that stated in the above title?
1) An attractive external presentation, an up-to-date and
consistent nomenclature, and as few errors as possible in the
typography and figures. 2) Contributions with a high level of
scientific competence, with references to earlier review articles. The literature coverage should concentrate mainly on
the period since the cutoff point of the previous review collection, bearing in mind, however, that in bringing out the
most important features of a topic one must also refer (in an
up-to-date context) to older publications. With regard to
these two criteria, the Patai volume reviewed here has failed
badly in some parts.
Although the external presentation is very attractive, the
frequent switching between “sulphinyl” and “sulfinyl” is annoying. In the volume on sulfenic acids only one chapter was
allowed to use the “f” spelling, but here this applies to seven
of the chapters, with the additional complication that for
Chapters 7 and 8 the contents list on the cover uses “ph”
whereas the chapters themselves use “f”.
With regard to errors in the text and figures, the following
can be noted, without claiming the list to be complete: p. 89,
what about stoichiometry in the equation given here?; p. 93,
Section 11 : elemental sulfur converts a sulfinate to a thiosulfonate, not to a thiosulfinate ArS(= 0)SH; p. 133: in Figure 1 the assignment for H4,which is cited at the top of
page 135, is not shown; p. 193: electron distribution in
Scheme 17?; p. 204: Equation (42) has kindly been credited
to our group, but does not originate from here; p. 235, line
2: I-damantyl; p. 376: in formula 117 a CH, group is missing; p. 433, Scheme 1:according to Equation (9) the reaction
arrows go in the wrong direction (left side of the equation);
p. 455: the “sulfonyl nitrites” referred to in Equation (4)
contain neither a sulfonyl group nor a nitrite function;
p. 462: in Equation (29) two negative charges appear from
neutral molecules in the intermediate complex, then disappear again in the end products; p. 496, Scheme 6: hexavalent
carbon; p. 498, Scheme 1: pentavalent nitrogen, Reference
[25]: Heesing instead of Hessing; p. 534: the “dominant resonance structure” 18 seems questionable; p. 538, Equation
(1 6) :in the text the reaction is described as a photooxidation,
whereas in the equation for the reaction the reaction conditions are given as H,O,/HOAc/6O0C; p. 542 discussing
Ref. [87]: the oxidations are carried out using oxaziridines,
not azyridines; p. 548, Figure 3: in ten formulas the positions
of the 13C NMR signals are not shown beside the correct
carbon atoms; p. 552: Equation (47) indicates a baffling
stoichiometry involving ethane; p. 597 : diazomethane is givAngew. Chem. Int. Ed. Engl. 30 (1991) No. 6
en as CH,N,; p. 597, Scheme 4: the decomposition of
sulfinyl peroxide must produce tert-butoxy, not tert-butyl
radicals, especially in view of the fact that tert-butyl alcohol
then appears as a reaction product; p. 611, Equation (27):
BF?; Equation (28): the positive charge is missing from the
ylid sulfur atom; Equation (32): according to the text the
action of elemental sulfur gives sulfinamides, but the origin
of the amide function is not explained; p. 612: formula 19
leads to an oxygen atom with an electron deficit; p. 615,
Scheme 2, the second and third lines of the formula are
barely understandable; p. 617, top line: “chain carrier
ArN.” should probably read ArNH; p. 618, Equation (46):
amyl nitrite is shown as the corresponding nitro compound;
p. 619, Equation (48): here a phenyl group has become a
phosphane; Equation (49): the nitrogen atom is missing
from the educt, but then appears in the intermediate and
end-product; p. 620, Equation (53): m-chloroperbenzoic
acid is abbreviated as CPA; in Equation (55) a hydrogen
transfer is shown (by the curved arrow) as taking place onto
the group R2 instead of onto the triple bond; p. 659, formula
14: the OH group in the ortho position is missing. Of the
entire volume Chapter 20 in particular is really annoying.
Also many of the chapters are less up-to-date than one
would wish. For example, only seven of the 23 chapters
include a reference to Volume E 11 of Houben-Weyl, which
was published in 1985 and contains the most recent comprehensive review to date of this class of compounds. In
many of the chapters the proportion of literature references
that relate to publications later than 1980 is about 10%; for
certain chapters that may be justified, but for many it is not.
This reviewer has some experience in the field of sulfinic acid
chemistry, and has to disagree with many of the statements
in the book. For example, it is claimed on page 3 that an
intermolecular substitution of a sulfinate at the saturated
carbon atom (p. 3) is not possible either for sulfones or for
sulfinyloxy compounds. This is certainly true under normal
circumstances, but is not an absolute rule (e.g. sulfones:
D. T. Gibson, J Chem. SOC.
1937, 1509; B. G. Boldyrev et
al., Zh. Org. Khim. 11 (1975) 455; sulfinyloxy compounds:
K. Schank, Houben- Weyl Bd. E l l (1985), p. 1148; pp. 1260,
1278 for sulfones). Zntramolecular substitution of a sulfinate
from a sulfone is cited (Ref. [14]) as occurring only under
fairly brutal conditions; however, this must be compared
with the synthesis of trans-chrysanthemum acid methyl ester
(see L.-F. Tietze, Th. Eicher: Reaktionen und Synthesen im
organisch-chemischen Praktikum, Thieme, Stuttgart 1981,
p. 433), which was achieved in 72 h in DMF at room temperature. On page 318 mesomerism is confused with tautomerism, but it suffers this fate again and again, as it is often
explained in terms of resonance. Nevertheless it always causes pain anew to a former student of B. Eistert, the author of
the book “Tautomerie und Mesomerie”. On page 456 the
pioneering work of Barnurd is mentioned (Ref. [I I]), but
without the important information that 1 mol of methylbenzenesulfenate requires only 0.7 mol of ozone to become
quantitatively oxidized to methylbenzenesulfinate; 30,is
not capable of effecting the oxidation under these reaction
conditions. On page 579 the reader is introduced to only two
basically different methods for synthesizing sulfinyl chlorides: a)replacement of OH (or ONa) by C1, and b) the
chlorinating oxidation of sulfanes or disulfanes. One can
excuse the fact that the citation given here ([Ref. 201) only
refers to Herrmann’s rediscovery of the method that we described using disulfide and sulfuryl chloride (W. Miiller, K.
Schank, Chem. Ber. ill (1978) 2870), since Herrmann also
did not cite our work. However, the omission of the method
for synthesizing sulfinyl chlorides by reacting thionyl chlo-
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