Liquid-phase oxidation of sulfides by an aluminum (and titanium) tert-butoxide - tert-butyl hydroperoxide system

Article abstract of DOI:10.1007/s11172-005-0026-9

A system aluminum (and titanium) tert-butoxide-tert-butyl hydroperoxide (1 : 2) under mild conditions (20°C, 1 h) oxidizes aliphatic and alkylaromatic sulfides and diphenyl sulfide to the corresponding sulfones in yields close to ～100%. The oxidation is induced by electron-excited dioxygen formed upon thermal decomposition of intermediate metal-containing peroxy trioxides (ozonides). The latter are formed as a result of the reversible reaction of aluminum or titanium tert-butoxides with tert-butyl hydroperoxide followed by the interaction of di-tert-butoxy-tert-butylperoxyaluminum and tri-tert-butoxy-tert-butylperoxytitanium that formed with another Bu ^tOOH molecule. Alkminum-containing peroxide (Bu^tO) ₂AlOOBu^t oxidizes sulfides to sulfoxides.

Full text of DOI:10.1007/s11172-005-0026-9

Russian Chemical Bulletin, International Edition, Vol. 53, No. 8, pp. 1729—1734, August, 2004
1729
Liquidꢀphase oxidation of sulfides by an aluminum (and titanium)
tertꢀbutoxide—tertꢀbutyl hydroperoxide system
ꢀ
V. A. Dodonov, E. A. Zaburdaeva, and L. P. Stepovik
N. I. Lobachevsky Nizhny Novgorod State University,
23 prosp. Gagarina, 603950 Nizhny Novgorod, Russian Federation.
Fax: +7 (831 2) 65 8592. Eꢀmail: zaea4@rambler.ru
A system aluminum (and titanium) tertꢀbutoxide—tertꢀbutyl hydroperoxide (1 : 2) under
mild conditions (20 °C, 1 h) oxidizes aliphatic and alkylaromatic sulfides and diphenyl sulfide
to the corresponding sulfones in yields close to ~100%. The oxidation is induced by electronꢀ
excited dioxygen formed upon thermal decomposition of intermediate metalꢀcontaining peroxy
trioxides (ozonides). The latter are formed as a result of the reversible reaction of aluminum or
titanium tertꢀbutoxides with tertꢀbutyl hydroperoxide followed by the interaction of diꢀtertꢀ
butoxyꢀtertꢀbutylperoxyaluminum and triꢀtertꢀbutoxyꢀtertꢀbutylperoxytitanium that formed
with another ButOOH molecule. Aluminumꢀcontaining peroxide (ButO)2AlOOBut oxidizes
sulfides to sulfoxides.
Key words: sulfides, sulfones, aluminum and titanium tertꢀbutoxides, tertꢀbutyl hydroperꢀ
oxide, oxidation, metalꢀcontaining trioxides, electronꢀexcited dioxygen.
The oxidation of sulfides by such strong agents as
peroxy acids and by a series of mineral oxidants (nitric
acid, chlorine dioxide, and others) includes their subseꢀ
quent transformation into sulfoxides and then into sulꢀ
fones. The synthesis of sulfones in the individual state
needs, as a rule, drastic conditions: prolonged heating
and excess oxidant.1,2
We have shown3 that the triꢀtertꢀbutoxyalumiꢀ
num (1)—tertꢀbutyl hydroperoxide (2) system even at
room temperature oxidizes dibenzyl and diphenyl sulfides
in benzene to the corresponding sulfones in 80—96%
yields.
It has been found4,5 that the reaction of alkoxide 1 and
2 equivalents of peroxide 2 in C6H6 or CCl4 results in
oxygen evolution in a yield >80%. Oxygen is formed due
to several consecutive reactions (Scheme 1). In the first
step, alkoxide 1 reacts reversibly with ButOOH (2) to
form diꢀtertꢀbutoxyꢀtertꢀbutylperoxyaluminum (3). The
latter reacts with the second molecule of peroxide 2 in a
sixꢀmembered reaction complex with the intermediate
formation of an aluminumꢀcontaining ozonide, viz.,
diꢀtertꢀbutoxyꢀtertꢀbutyltrioxyaluminum (4).
The existence of aluminumꢀcontaining ozonide 4 is
confirmed by its parallel homolytic decomposition reꢀ
sulting in oxygenꢀcentered radicals ButO•, ButOO•,
(ButO)2AlO•, and (ButO)2AlOO• identified by ESR usꢀ
ing spin traps.5
The thermal decomposition of trioxide 4 is assumed5
to occur due to the intramolecular transfer of the ButO
group (with an electron pair or, which is more probable,
as a radical) to the Al atom (SR2 substitution). According
to the spin conservation rule, singlet dioxygen is evolved.
Its yield was determined by the reactions with anthracene
and 9,10ꢀdimethylanthracene and equaled to 40% in benꢀ
zene and 50% in CCl4. It should be taken into account
that free radicals escaping to the solvent bulk are effiꢀ
ciently involved in quenching of electronꢀexcited oxygen.5
The purpose of this work is to study the oxidation of
typical representatives of aliphatic, alkylaromatic, and aroꢀ
matic sulfides by electronꢀexcited dioxygen generated by
systems 1—2 and tetraꢀtertꢀbutoxytitanium (5)—2 in benꢀ
zene at room temperature. It was of interest to compare
the reactivities of dioxygen formed in these systems and
Scheme 1
1
singlet oxygen O2(∆g) obtained by photoinduced exciꢀ
tation.
Experimental
Commercial solvents (analytical and reagent grades) were
used. Benzene was purified by distillation from P2O5 and stored
over metallic sodium; chlorobenzene and CCl4 were distilled
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1663—1668, August, 2004.
1066ꢀ5285/04/5308ꢀ1729 © 2004 Springer Science+Business Media, Inc.

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Russ.Chem.Bull., Int.Ed., Vol. 53, No. 8, August, 2004
Dodonov et al.
and stored over Na2SO4. Dimethyl, diphenyl, and methyl pheꢀ
nyl sulfides (pure) were distilled before use. Dibenzyl sulfide
(pure) was recrystallized from ethanol, and anthracene ("scinꢀ
tillation") was recrystallized from benzene. Dialkyl sulfides were
synthesized by the reaction of Na2S with the corresponding
alkyl halides according to a described procedure.6 The method
of synthesis and properties of aluminum triꢀtertꢀbutoxide (1)
have been described previously.5 Diꢀtertꢀbutoxyꢀtertꢀbutylperꢀ
oxyaluminum was synthesized by the reaction of diꢀtertꢀbutoxyꢀ
aluminum chloride with ButOOH in the presence of Et2NH.7
The content of the main substance was 90—96%. Diꢀtertꢀbutoxyꢀ
aluminum chloride is the product of the treatment of a solution
of alkoxide 1 in benzene with anhydrous HCl.8 Titanium tetraꢀ
tertꢀbutoxide was synthesized by a known procedure.9 All proceꢀ
dures with aluminum and titanium derivatives were carried out
in an atmosphere of dry oxygenꢀfree argon. tertꢀButyl hydroperꢀ
oxide was synthesized according to a described procedure.10 The
content of active oxygen in ButOOH was 99.5—99.8%.
(1.4 mmol) and Bn2SO (0.5 mmol) were isolated. In addition,
ButOH (1.9 mmol) was found in the aqueousꢀacidic layer.
Results and Discussion
Sulfides R1SR2 (6a—h) and Ph2S (6i), which does not
react with O2(1∆g),12 were chosen for the study. They
were oxidized by the system 1—2 using either an equimoꢀ
lar amount of peroxide 2 or its twofold excess in benzene
at room temperature. In the latter case, the only reaction
products were sulfones 7a,c—i (Scheme 2, Table 1).
Scheme 2
IR spectra were recorded on a SpecordꢀM80 instrument in
an interval of 4000—400 cm–1. Volatiles (ButOH, Me2S, MeSEt,
and Et2S) were analyzed by GLC on an LKhMꢀ80 chromatoꢀ
graph (helium as a carrier gas, column 120 cm long, 30% dinonyl
phthalate on Chromaton NꢀAWꢀDMCS). The temperature was
varied within 50—120 °C. The chromatographic analysis of Pr2S,
Pri2S, and Bu2S, as well as Pr2SO2, Pri2SO2, and Bu2SO2, was
carried out on a Tsvetꢀ2ꢀ65 instrument (flameꢀionization detecꢀ
tor, helium as a carrier gas, column 300 cm long, ApiesonꢀL,
15% on the support indicated above, temperature 150—180 °C).
Anthracene, Ph2S, and MeSPh were analyzed on the same inꢀ
strument (column 300 cm long, 5% SEꢀ30 on Inerton Super) at
180—270 °C.
a
b
c
d
e
Pri
Pri
f
g
h
i
R1
R2
Me Me
Me Et
Et
Et
Pr
Pr
Bu Me Bn
Bu Ph Bn
Ph
Ph
Sulfones are formed during mixing accompanied by
noticeable selfꢀheating of the reaction mixture. After
10 min, 50% Pr2SO2 were found chromatographically.
The reactions are completed within an hour in high yields
(79—96%).
When using a twofold excess of peroxide 2, the system
of titanium tetraꢀtertꢀbutoxide (5)—ButOOH (2) oxidizes
sulfides 6d,f,h under similar conditions and with the same
rate and efficiency (Scheme 3).
Qualitative analysis for sulfoxides was carried out according
to a published procedure.11
Oxidation of dipropyl sulfide by the (ButO)3Al (1)—ButOOH
(2) system (1 : 2). Peroxide 2 (16 mmol) was added to a solution
of compound 1 (8 mmol) and Pr2S (8 mmol) in benzene (20 mL).
After 1—2 min, the reaction mixture selfꢀheated. The formation
of Pr2SO2, whose amount achieved 5.2 mmol in 4.5 h, was
monitored by GLC. Then the solvent and volatile components
of the reaction mixture were condensed in a trap cooled
with liquid nitrogen. The volatile fraction contained ButOH
(11.4 mmol) and ButOOH (0.2 mmol). Sulfuric acid (10%) was
added to a colorless powderꢀlike residue, the mixture was exꢀ
tracted with Et2O, and the extract was dried with Na2SO4
and analyzed by GLC. Pr2SO2 (94%, 7.5 mmol), ButOH
(20.7 mmol), and ButOOH (1.2 mmol) were found.
Scheme 3
The corresponding sulfones were the single products
in all entries. According to the GLC data, the yields of
Pr2SO2 and Bu2SO2 were 85—99%.
Other sulfides were oxidized similarly.
Etherꢀinsoluble but waterꢀsoluble Me2SO2, Et2SO2, and
Pri2SO2 were isolated by the treatment of the reaction mixture
with AcOH taken in an exactly calculated amount. Aluminum
acetate that formed was filtered off, and volatile components
were removed under a reduced pressure.
Oxidation of dibenzyl sulfide by an equivalent amount of diꢀ
tertꢀbutoxyꢀtertꢀbutylperoxyaluminum (3). (ButO)2AlOOBut (3)
(2.1 mmol), Bn2S (2.1 mmol), and benzene (10.5 mL) were
mixed. Then the solvent and volatiles were condensed in a trap
cooled with liquid nitrogen. The volatile fraction contained
ButOH (1.4 mmol). Sulfuric acid (10%) was added to the resiꢀ
due, the mixture was extracted with Et2O, and the extract was
dried with Na2SO4 and analyzed by GLC. ButOH (2.7 mmol)
and ButOOH (0.1 mmol) were found. Then unreacted Bn2S
All sulfones were isolated in the individual state. The
IR spectra correspond to those of authentic samples.13
Electronꢀexcited dioxygen seems to be the oxidant of
the S atom of sulfide. The data of several works14—17
performed in our laboratory show that dioxygen evolved
is consumed to the oxidation of C—H groups. The methylꢀ
ene groups of alkanes, alkylarenes, ketones, etc. are transꢀ
formed into carbonyl groups by ketonization, whereas
methine groups are transformed into hydroperoxy groups.
The CH2 groups in the benzyl and allyl fragments are
oxidized especially easily.16,17 The oxidation is accompaꢀ

Lowꢀtemperature oxidation of sulfides
Russ.Chem.Bull., Int.Ed., Vol. 53, No. 8, August, 2004
1731
Table 1. Oxidation of sulfides 6a—i by the (ButO)3Al (1)—ButOOH (2) systema
Entry
Sulfide
Products/mole per mole of sulfideb
volatile fraction after hydrolysis of a nonvolatile residue
ButOOH ButOH
R1SR2
ButOOH ButOH R1SR2
R1SO2R2
1 c
6a
6c
6d
6e
6f
6g
6h
6i
0.04
0.06
0.06
0.08
0.05
0.04
0.05
—
2.26
2.30
1.73
2.16
2.40
1.96
2.29
2.24
0.69
1.95
0.72
0.04
Traces
Traces
—
—
0.05
—
0.03
—
1.62
—
—
—
Traces
—
0.034
0.02
—
0.12
—
0.94
0.79
0.96
0.95
0.96
0.93
0.96
0.80
0.17
0.20
0.41
d
d
2 c
3 c
0.15
2.22
4 c
—
—
d
d
5 c
0.14
0.04
0.22
—
1.92
2.38
6 c
7 c
—
d
8 c
—
2.46
2.19
9 e,f
10 e,f
11 e,f
6a
6b
6d
0.02
0.08
0.06
0.44
0.28
0.23
0.15
d
d
—
—
—
0.16
0.26
2.06
a 20 °C, solvent: benzene (entries 1, 3—5, 7—11), chlorobenzene (entry 2), and CCl4 (entry 6).
b Averaged data are presented.
c 1 equiv. of (ButO)3Al + 2 equiv. of ButOOH.
d Not determined.
e 1 equiv. of (ButO)3Al + 1 equiv. of ButOOH.
f The corresponding sulfoxides were qualitatively identified in entries 9—11.
nied by the cleavage of the C—C bonds in the organic
substrate. Photoinduced dioxygen O2(1∆g) does not react
with C—H bonds in hydrocarbons. Thus, the oxidating
system 1—2 is a more efficient oxidant.
Sulfides can be oxidized by oxidating systems based
on ButOOH and alkoxides 1 or 5 directly under the acꢀ
tion of ButOOH or metalꢀcontaining peroxides of the
(ButO)nMOOBut type (M = Al, n = 2; M = Ti, n = 3),
which are present in the reaction mixture (see Scheme 1).
It is established that peroxide 2 does not oxidize sulꢀ
fides under the reaction conditions. To reveal how metalꢀ
containing peroxides are involved in oxidation, we studꢀ
ied the interaction of a series of sulfides (6d,f,h,i) with
aluminumꢀcontaining peroxide 3. The results are preꢀ
sented in Table 2.
According to the data from this study, the main reacꢀ
tion products at an equimolar sulfide : peroxide 3 ratio are
sulfoxides 8d,f,h,i, which were qualitatively identified in
all experiments. Sulfoxides 8h,i were isolated in yields of
22 and 19%, respectively. It should be noted that only a
half of sulfide is oxidized, while ~30% are oxidized in the
case of diphenyl sulfide. No sulfones were found. Sulfoxꢀ
ides are formed, probably, due to the nucleophilic attack
of the peroxy group on the S atom. The attack is favored
by the coordination of sulfide with the Al atom as an
Sꢀligand18 (Scheme 4).
Table 2. Oxidation of sulfides 6d,f,h,i by diꢀtertꢀbutoxyꢀtertꢀbutylperoxyaluminum (3)
(1 equiv.)a
Sulfide
(R2S)
R
Products/mole per mole of sulfideb
volatile fractionc
after hydrolysis of a nonvolatile residue
ButOH
R2S ButOOH ButOH
R2S
R2SO R2SO2
d
6d
6f
6h
6i
Pr
Bu
Bn
Ph
0.71
0.59
0.62
0.32
0.41
0.29
—
0.25
0.37
0.06
0.14
2.04
1.86
2.03
2.00
0.10
0.29
0.67
0.71
—
—
—
0.10
—
d
0.22
0.19
—
—
a 20 °C, benzene.
b Averaged data are presented.
c Traces of ButOOH are present.
d Qualitative determination.

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Dodonov et al.
Scheme 4
higher nucleophilicity of hydroperoxide 2 over that of
ButOH or water20 and, hence, the peroxide anion ButOO–
is a stronger nucleophile than the corresponding anions
ButO– or HO–. All these facts cause the formation of
peroxides of the (ButO)nMOOBut type (M = Al, n = 2;
M = Ti, n = 3), which react with the second molecule of 2
in a sixꢀmembered reaction complex involving, for exꢀ
ample, an Al atom (innerꢀsphere reaction),21 and the
strong ButO base eliminates a proton to form trioxide 4
(Scheme 6).
R = Pr (d), Bu (f), Bn (h), Ph (i)
Scheme 6
Simultaneously aluminumꢀcontaining peroxide 3 therꢀ
mally decomposes, which followed from the detection of
ButOH in the volatile fraction.8
In all cases, a twofold increase in the amount of perꢀ
oxide 3 results in the corresponding sulfones 7 through
the intermediate formation of sulfoxides 8. The S atom in
the latter is more electrophilic and, as a consequence,
more active toward peroxide 3, which acts as a nucleoꢀ
philic agent (Scheme 5).
Thus, the physicochemical activation of dioxygen ocꢀ
curs in the systems under study (see Schemes 1 and 6).
Dioxygen is evolved in the catalytic cycle, which is conꢀ
firmed by the independent reactions of peroxides 2 and 3
and by the oxidation of Ph2S and Bn2S.3
Scheme 5
The energy of dioxygen formation calculated from the
dissociation energies of covalent bonds of aluminum
peroxytrioxide exceeds that of the first excitation state
O2(1∆g) and equals 43.5—51.45 kcal mol–1. The standard
dissociation energy of O2(3Σg–) equal to 118 kcal mol–1
was taken into account in the calculations, and the O—O
Thus, the reaction of peroxide 3 with Ph2SO is comꢀ
pleted by the formation of Ph2SO2 in 86% yield.
The data presented indicate that peroxide 3 reacts with
sulfides and sulfoxides as a nucleophilic reagent, while it
reacts with ButOOH directly (see Scheme 1) to form
metalꢀcontaining ozonide 4, due to which the direction
of sulfide oxidation changes.
This conclusion is confirmed by the results of the oxiꢀ
dation of dimethyl, ethyl methyl, and dipropyl sulfides
6a,b,d by the system 1—2 in benzene at an equimolar
ratio of reactants 1, 2, and the sulfide (see Table 1, enꢀ
tries 9—11). Under these conditions, the yield of sulfones
is halved (<41%). In addition to the sulfones, unconsumed
sulfides were isolated, and the corresponding sulfoxides
8a,b,d were qualitatively identified. In this case, the twoꢀ
fold decrease in the yield of sulfones is a result of the
adequate decrease in aluminumꢀcontaining ozonide 4,
which is an efficient oxidant of sulfides.
The lowꢀtemperature oxidation of organic substrates
by the system 1—2 and oxidation by hydroperoxides cataꢀ
lyzed by compounds of `transition and nontransition metꢀ
als occur due to the intermediate formation of metalꢀ
containing peroxides in 10—90% yields during the time
from fractions of a second to several minutes.19
In the studied reactions of sulfide oxidation by the
systems 1—2 and 5—2, the formation of metalꢀcontainꢀ
ing aluminum and titanium peroxides is determined by a
bond energy in hydrogen peroxide is 44—51 kcal mol–1 21
.
To compare the data on the reactivity of dioxygen
generated by the systems under study and that of singlet
oxygen O2(1∆g) generated by photoirradiation, we used
the known results22,23 indicating that O2(1∆g) oxidizes
sulfides to sulfoxides according to Scheme 7.
Scheme 7
Minor amounts of sulfone were also found among the
reaction products. Unlike aliphatic sulfides, Ph2S is not
oxidized by singlet oxygen under these conditions. Howꢀ
ever, as mentioned previously,22,23 Ph2S is oxidized to
Ph2SO only in a mixture with Et2S. Based on the experiꢀ
mental kinetic data and quantumꢀchemical calculaꢀ
tions,24,25 we assumed that the oxidation proceeds via
peroxide intermediates (Scheme 8).
Intermediate 9 (probability of its formation is preferꢀ
ential) oxidizes the next molecule of the starting sulꢀ
fide, including Ph2S, to the corresponding sulfoxide
(Scheme 9).

Lowꢀtemperature oxidation of sulfides
Russ.Chem.Bull., Int.Ed., Vol. 53, No. 8, August, 2004
1733
noted27 that the physical deactivation of O2(1Σg+) occurs
simultaneously, under any conditions of its transition state,
to form O2(1∆g). This is favored by the lability of the
reagent, its spinꢀallowed or ꢀforbidden transition, deactiꢀ
vation due to collisions with solvent molecules, etc.
Electronꢀexcited dioxygen generated by the systems
1—2 and 5—2 reacts with sulfide not as a kinetically indeꢀ
pendent molecule in the solvent bulk but oxidizes the
substrate to sulfone directly in the coordination sphere of
the metal with the intermediate formation of thiadioxirane
10 (Scheme 12).
Scheme 8
Scheme 9
Scheme 12
Thiadioxirane 10, whose stability is favored by aprotic
solvents,12,22 is responsible for the formation of sulfones.
The yield of the latter is much lower than that of sulfoxꢀ
ides. It should be noted that, when reacting in benzene,
thiadioxirane 10 decomposes to the starting sulfide and
dioxygen in the triplet state O2(3Σg–) (Scheme 10).
M = Al, n = 3; M = Ti, n = 4
We cannot exclude another alternative route of sulꢀ
fone synthesis: the direct oxidation of sulfide by ozonide 4
in the step of formation of radical pairs (ButO)2AlOO•
and ButO•. The oxidation of coordinated sulfide is acꢀ
companied by the elimination of electronꢀexcited diꢀ
oxygen during the intramolecular SR2 substitution of the
ButO radical at the metal atom without oxygen escape to
the solvent bulk.
Scheme 10
Our hypothesis was checked for the oxidation of Pr2S
by system 1—2 (1 : 2) in benzene in the presence of anꢀ
thracene. In this reaction, the yield of Pr2SO2 was ~100%,
and anthracene was isolated from the reaction mixture in
an unchanged state. This fact indicates that electronꢀexꢀ
cited dioxygen does not escape to the solvent bulk, under
these conditions, but reacts with sulfide directly in the
coordination sphere of the Al atom.
In addition, for Bn2S oxidation, one could assume the
oxidation of the C—H bonds in the methylene groups
followed by sulfide degradation to benzaldehyde, which
occurs when this substrate is oxidized by O2(1∆g).28 No
products of the oxidation of C—H bonds were found when
Bn2S was oxidized by the systems 1—2 and 5—2.
Thus, the reactivity of photoinduced O2(1∆g) differs
sharply from that of electronꢀexcited dioxygen formed by
the reaction of alkoxide 1 or 5 with ButOOH with the
intermediate formation of the corresponding trioxides
(ozonides) (see Scheme 1). The conversion of singlet
dioxygen to the triplet in the liquid phase is especially
intense, as known, in the presence of paramagnetic speꢀ
cies (Scheme 11).
Scheme 11
It should be noted in conclusion that sulfones are
formed by the action of electronꢀexcited dioxygen withꢀ
out its escape to the solvent bulk and involving sulfide in a
reaction complex. Therefore, some sulfides, in particular,
Pr2S and Ph2S, can be used as the test reagents to elecꢀ
tronꢀexcited states of oxygen in the liquid phase. These
compounds, unlike substituted alkenes, dienes, anꢀ
thracenes,5,26 and others, have donor S atoms with a low
electronegativity and, hence, a high polarizability. They
form, as known,18 stable complexes with "soft" metal ions,
and coordination bonds in these complexes are characꢀ
terized by a considerable covalent contribution. All these
facts result in the easy oxidation of sulfides through the
The average lifetime of the O2(1Σg+) state is
10–11—10–10 s, and that of the O2(1∆g) state is longer by
four—five orders of magnitude.26 Naturally, the chemical
properties of singlet dioxygen molecules should differ from
both each other and those in the triplet state. Photoꢀ
chemical studies of dioxygen O2(1∆g) concerning its reacꢀ
tions with different substrates, such as alkenes, dienes,
furan derivatives, anthracenes, etc., have been performed
to date.27 As for the electronꢀexcited state O2(1Σg+), the
results obtained exclude unambiguously any chemical reꢀ
actions with the substrates listed above. It has also been

1734
Russ.Chem.Bull., Int.Ed., Vol. 53, No. 8, August, 2004
Dodonov et al.
13. W. R. Feairheller, Jr., and J. E. Katon, Spectrochim. Acta,
1964, 20, 1099.
14. V. A. Dodonov, L. P. Stepovik, A. S. Soskova, and E. A.
Zaburdaeva, Zh. Obshch. Khim., 1994, 64, 1715 [Russ. J. Gen.
Chem., 1994, 64 (Engl. Transl.)].
15. L. P. Stepovik, E. A. Zaburdaeva, and V. A. Dodonov,
Zh. Obshch. Khim., 1997, 67, 282 [Russ. J. Gen. Chem., 1997,
67 (Engl. Transl.)].
16. V. A. Dodonov, E. A. Zaburdaeva, N. V. Dolganova, L. P.
Stepovik, and T. I. Zinov´eva, Zh. Obshch. Khim., 1997, 67,
988 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].
17. I. M. Martynova, L. P. Stepovik, and V. A. Dodonov,
Zh. Obshch. Khim., 2001, 71, 1681 [Russ. J. Gen. Chem.,
2001, 71 (Engl. Transl.)].
intermediate formation of persulfoxides 9 and thiaꢀ
dioxiranes 10 responsible for the formation of the target
products. Sulfoxides and sulfones are synthesized very
rapidly and specifically in high yields, as well as without
secondary reactions.
The authors thank O. S. Morozov for recording and
interpretation of IR spectra.
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Received October 24, 2003;
in revised form February 2, 2004