812

Solvent-free and selective tosylation of alcohols

and phenols with p-toluenesulfonyl chloride by
heteropolyacids as highly efficient catalysts
Razieh Fazaeli, Shahram Tangestaninejad, and Hamid Aliyan

Abstract: Tosylation of some alcohols and phenols has been directly carried out with p-toluenesulfonyl chloride using
heterodoxy acids (H3PW12O40, H3PMo12O40, AlPW12O40, and AlPMo12O40) as catalysts in the absence of solvent. We
found that heteropoly acids AlPW12O40 and AlPMo12O40 were effective catalysts for the tosylation of alcohols and phe-
nols. In the case of aliphatic alcohols, secondary alcohols undergo tosylation chemoselectively in the presence of pri-
mary hydroxyl groups. This new method consistently has the advantage of excellent yields and short reaction time.
Key words: tosylation, p-TsCl, Keggin-type polyoxometalate, solvent-free reaction.

Résumé : La réaction de tosylation de quelques alcools et phénols a été réalisée directement par réaction avec du chlo-
rure de p-toluènesulfonyle en utilisant des acides hétérodoxes (H3PW12O40, H3PMo12O40, AlPW12O40 et AlPMo12O40)
comme catalyseurs, en l’absence de solvants. On a trouvé que les hétéropolyacides AlPW12O40 et AlPMo12O40 sont des
catalyseurs efficaces pour la tosylation des alcools et des phénols. Dans le cas des alcools aliphatiques, les alcools se-
condaires subissent une tosylation chimiosélective lorsqu’ils sont en présence de groupes hydroxyles primaires. Cette
nouvelle méthode présente les avantages d’excellents rendements et de temps de réaction courts.
Mots clés : tosylation, chlorure de p-tosyle, polyoxométallate de type Keggin, réaction sans solvant.
[Traduit par la Rédaction] Fazaeli et al. 818

Introduction cohols give rearranged or polymeric products. Also, in this

Tosylation of alcohols is an important transformation in
organic synthesis (1, 2). The most widely used reagents, p-
toluenesulfonyl chloride (p-TsCl) or anhydride, are reactive
in comparison with p-toluenesulfonic acid (3). Preparation
of sulfonates generally relies on the use of the corresponding
sulfonyl chloride or anhydride in the presence of pyridine
(3b, 4), triethylamine (3a, 3c), 1,4-diazabicyclo[2.2.2]octane
(DABCO) (3d), or an aqueous base.
p-Toluenesulfonic acid (p-TsOH) has also been used (5)
as a tosylating agent, but in this case, expensive reagents
such as trialkyl orthoformates, alkylethers, esters, or 2-
alkoxybenzothiazolium salt are also necessary. Organic base
adducts of sulfonyls such as aryl sulfonyl methylimidazo-
lium salts, 1-phenylsulfonyl benzotriazole, and 1-(benzene-
sulfonyl)- and 1-(p-toluenesulfonyl)-3-methylimidazolium
triflates have also been employed for sulfonate synthesis (6).
The formation of the side products using these reagents in
the presence of a base is also a problem (1, 3b, 5).
Fe3+-montmorillonite clay has been reported to catalyze
the tosylation of alcohols with p-TsOH (7). This catalyst is
effective for tosylation of aliphatic alcohols, but aromatic al-
Received 7 November 2005. Published on the NRC Research
Press Web site at http://canjchem.nrc.ca on 17 May 2006.
R. Fazaeli and S. Tangestaninejad.1 Department of
Chemistry, Isfahan University, Isfahan, 81746-73441, Iran.
H. Aliyan. Department of Chemistry, Shahreza Islamic Azad
University 31186145, Shahreza, Isfahan, Iran.
1
Corresponding author (e-mail: stanges@sci.ui.ac.ir).
case, primary and secondary alcohols behaved very simi-
larly. CoCl2·6H2O (8), silica chloride (9), and ZrCl4 (10)
have also been used to catalyze the tosylation of both
aliphatic and aromatic alcohols with p-TsOH. In these meth-
ods, tosylation of long-chain alcohols required longer reac-
tion times and the yields were poor.
Selective tosylation of a primary hydroxyl group in a mol-
ecule containing primary and secondary hydroxyl groups is
often required. The resulting sulfonates are the precursors
for epoxides enroute to the synthesis of a number of natural
products and drugs (11). It is important to realize a high
regioselectivity in the initial sulfonylation step to obtain
epoxides with high purity via cyclization of the product
hydroxyl sulfonates. Thus, there are a limited number of
suitable direct tosylation methods for alcohols with p-TsOH
and there is still a need to develop efficient protocols for this
purpose.
Herein, we wish to report a suitable method for direct
tosylation of alcohols with p-TsCl catalyzed by polyoxo-
metalates as Lewis acid catalysts (Scheme 1).
Polyoxometalates belong to a large class of nanosized
metal–oxygen cluster anions. The chemistry of polyoxo-
metalates (heteropolyacids and heteropolysalts), started by
Berzelius back in 1826, has now reached maturity. But it is
still a rapidly developing field interconnected with many dis-
ciplines (12).
The applications of polyoxometalates (POMs, especially
polyoxotungstates) for environmental protection and remedi-
ation have attracted much attention in recent years (13–19).
The majority of POMs have structures composed of molyb-

Can. J. Chem. 84: 812–818 (2006) doi:10.1139/V06-066 © 2006 NRC Canada

Fazaeli et al.
Scheme 1.
p -TsCl, POM
R-OH R-OTs
Solvent-free, r.t.
POM = HTP, HMP, AlTP, AlMP
denum and tungsten polyhedrons. Other elements occur in
small amounts in these structures. Polyoxotungstates and
polyoxomolybdates decompose in alkaline media to form
simple tungstate and molybdate ions, and therefore, they can
be determined in these forms (20).
The relative activity of Keggin heteropolyacids primarily
depends on their acid strength. Other properties, such as the
oxidation potential as well as the thermal and hydrolytic sta-
bility, are also important.
Tungsten heteropolyacids are usually the catalysts of
choice because of their stronger acidity, higher thermal sta-
bility, and lower oxidation potential compared with molyb-
denum acids. Generally, if the reaction rate is controlled by
the catalyst acid strength, H3PW12O40 shows the highest cat-
alytic activity in the Keggin series. The acids H3PW12O40,
(HTP) and H3PMo12O40, (HMP) are readily available and
most frequently used as catalysts. These acids have rela-
tively high thermal stabilities and decompose at 465 and
375 °C, respectively (12).
Preparation of aluminum dodecatungstophosphate
(AlPW12O40) was reported in 1982 by Ono (21) from the re-
action of aluminum nitrate and dodecatungstophosphoric
acid in a quantitative yield. We have also prepared aluminum
dodecatungstophosphate (AlPW12O40 or AlTP) and alumi-
num dodecamolybdophosphate (AlPMo12O40 or AlMP) by
the addition of aluminum nitrate or aluminum carbonate to
the aqueous solution of tungstophosphoric acid or moly-
bdatophosphoric acid, respectively, which on complete evap-
oration of water gave the desired compound as white (AlTP)
and yellow (AlMP) powders in quantitative yield. AlTP pre-
pared by both protocols gave satisfactory analytical results
within the range of the experimental error. This salt is a wa-
ter stable and nonhygroscopic compound (21–23).
Experimental
Tungstophosphoric acid and dodecamolybdophosphoric
acid (HTP and HMP), which are cheap, reusable, heteroge-
neous, and easily available catalysts, were purchased from
Merck and were purified by extraction with Et2O from the
aqueous solution of the acids. After evacuation at 150–
300 °C for 1 to 2 h under reduced pressure, pure HTP and
HMP were obtained (24). AlTP can be prepared from cheap
and commercially available chemicals in a quantitative yield
in aqueous media. In contrast to many other Lewis acids,
storage of this compound does not need special precautions,
e.g., it can be stored on a bench top for months without los-
ing its catalytic activity. In addition, as a nonhygroscopic,
noncorrosive, and water stable compound, handling of AlTP
is easy, which makes it a suitable catalyst for large-scale op-
erations.
813
All solvents were reagent grade. All reaction mixtures
were stirred magnetically and were monitored by TLC. IR
spectra were recorded on a PerkinElmer FT-IR Impact 400D
spectrophotometer with KBr. 1H and 13C NMR spectra were
recorded on a Bruker AW 500 MHz spectrometer.
General procedure for tosylation
The solvent-free method has an operationally simple pro-
cedure. An alcohol or phenol (1 mmol) and POM
(AlPW12O40, AlPMo12O40, H3PW12O40, or H3PMo12O40,
0.03 mmol) and p-TsCl (1.2 mmol) were ground together in
a mortar and pestle at room temperature for several minutes
to form the tosylates. In cases when the mixture stuck to the
walls of the mortar, it was taken off the walls with a spatula
and grounding was redone. The progress of the reaction was
monitored by GC and TLC. After complete disappearance of
the starting material, the mixture was poured into a satd.
NaHCO3 solution, extracted with CH2Cl2 (3 × 20 mL), and
the organic phase was dried over Na2SO4. The residue was
subjected to column chromatography over silica gel using
EtOAc–hexane (1:4) as eluent to produce pure tosylate. The
structures of the products were established from their spec-
tral (1H and 13C NMR, IR, and MS) data.
Selected spectroscopic data
Cyclopentyl p-toluenesulfonate (Table 1, n)
Thick oil. IR (film, cm–1): 1172, 1354. 1H NMR
(200 MHz, CDCl3) δ: 1.54–1.78 (8H, m, -[CH2]4-), 2.43
(3H, s, CH3), 4.49 (1H, m, CHO-), 7.32 (2H, d, m-H, J =
8.1 Hz), 7.78 (2H, d, o-H, J = 8.1Hz). MS (EI) m/z: 240
(M+, 2), 172 (61), 107 (33), 91 (100), 65 (34).
Cyclohexyl p-toluenesulfonate (Table 1, m)
Thick oil. IR (film, cm–1): 1170, 1351. 1H NMR
(200 MHz, CDCl3) δ: 1.30–1.78 (10H, m, -[CH2]5-), 2.44
(3H, s, CH3), 4.49 (1H, m, CHO-), 7.32 (2H, d, m-H, J =
8.8 Hz), 7.79 (2H, d, o-H, J = 8.8 Hz). 13C NMR (200 MHz,
CDCl3) δ: 143.99, 134.32, 129.38, 127.11 (Ar carbons),
81.12 (CHO), 31.90, 24.46, 22.92, 21.11 (alkane). MS (EI)
m/z: 254 (M+, 2), 173 (100), 155 (46), 91 (31), 82 (31), 67
(22), 65 (7).
Results and discussion
At first, to investigate the catalytic ability of hetero-
polyacids (H3PW12O40, H3PMo12O40, AlPW12O40, AlPMo12O40)
to act as catalysts on the tosylation of alcohols and phenols,
different alcohols and phenols were mixed with p-TsCl in
the presence of POMs to form the tosylates under solvent-
free conditions. The results showed that AlPW12O40 and
AlPMo12O40 show higher catalytic activity than the acid forms
in our experimental conditions (Tables 1 and 2). The cata-
lytic activities are as follows: AlPW12O40 ~ AlPMo12O40 ≥
H3PW12O40 > H3PMo12O40. The blank experiments, in the
absence of catalysts, showed that p-TsCl is much less effi-
cient in producing the tosylated products.
As shown in Tables 1 and 2, by using AlPW12O40 or
AlPMo12O40 as catalyst, primary, secondary, benzylic, and
allylic alcohols gave tosylated products in good yields.
Benzylic alcohols, such as benzyl, 2-nitrobenzyl, 4-
© 2006 NRC Canada
814 Can. J. Chem. Vol. 84, 2006

Table 1. Results on the tosylation of different alcohols using some heteropoly acids.

Time Yield
Entry Substrate Product Type of POM (min) (%)a,b,c
a HO TsO HTP 20 45
HMP 27 50
AlTP 7 100
AlMP 9 95
N N
b OH OTs HTP 25 50
HMP 31 55
C CH3 C CH3 AlTP 8 100
AlMP 8 98
H H

c HTP 20 60
OH OTs
HMP 25 45
AlTP 15 98
NO2 NO2
AlMP 18 78

d OH
HTP 20 50
OTs
HMP 25 55
O2N
AlTP 10 90
O2N
AlMP 14 95

e HTP 21 60
OH OTs HMP 28 60
CH3 CH3 AlTP 5 92
O O
AlMP 7 95

f HTP 20 55
OH OTs HMP 35 60
H3C H3C AlTP 7 98
O O AlMP 7 92

g OTs HTP 20 60
OH
HMP 30 55
AlTP 10 98
AlMP 10 98

h OH OTs HTP 20 60
HMP 20 55
AlTP 10 98
AlMP 11 93

i CH2OH CH2OTs HTP 20 60

HMP 30 55
AlTP 14 98
AlMP 17 98

j HTP 20 65
CH2OH CH2OTs HMP 25 65
AlTP 10 90
AlMP 10 95

k OH OTs HTP 25 60
HMP 25 50
AlTP 7 98
AlMP 13 89

nitrobenzyl, 3-methoxybenzyl, 4-methoxybenzyl, and 1-
phenylpropyl alcohol, were converted to the corresponding
tosylates in 78%–100% yields (Table 1, entries b–h). Simi-
larly, allylic alcohols, such as cinnamyl and geraniol alco-
hol, underwent tosylation to afford the corresponding
tosylates in 90%–98% yields (Table 1, entries i and j).
Aliphatic alcohols were more easily tosylated than aromatic
alcohols. However, long-chain alcohols, in the presence of
AlPW12O40 or AlPW12O40 as catalyst, were converted to the
desired products in moderate yields (Table 1, entries q–t,
73%–80%). Cholesterol (Table 1, entry o), which is a more
complex secondary alcohol, produced the tosylated product

© 2006 NRC Canada

Fazaeli et al. 815

Table 1. (continued).

Time Yield
Entry Substrate Product Type of POM (min) (%)a,b,c
l HTP 15 75
HMP 16 60
AlTP 9 96
OH OTs AlMP 9 90

m OH OTs HTP 20 65
HMP 20 50
AlTP 6 96
AlMP 9 90

n HTP 20 65
OH OTs HMP 25 65
AlTP 11 96
AlMP 17 90

o HTP 20 65
HMP 20 50
AlTP 6 96
AlMP 9 90

HO
TsO

OH OTs
n n

p n=2 n=2 HTP 55 60

HMP 55 45
AlTP 30 80
AlMP 38 75

q n=7 n=7 HTP 60 55

HMP 55 50
AlTP 30 80
AlMP 35 75

r n = 11 n = 11 HTP 50 50
HMP 50 50
AlTP 40 80
AlMP 48 75

s n = 13 n = 13 HTP 20 40
HMP 20 40
AlTP 11 75
AlMP 13 73

t n = 15 n = 15 HTP 55 45
HMP 60 40
AlTP 29 83
AlMP 48 75
H H
u HTP 60 65
HMP 20 55
H H AlTP 7 95
OH OTs AlMP 9 95
H
H

in high yield (90%–96%). Some phenols (Table 2) and ter- the case of diols, under the same reaction conditions, no
tiary alcohols (Table 1, entries u and v) undergo tosylation tosylate product was detected in the reaction mixture and
under the same experimental conditions. For aromatic alco- both hydroxyl groups remained intact in the presence of p-
hols, no rearranged or polymeric products were observed. In TsCl (Table 1, entries w–z).

© 2006 NRC Canada

816 Can. J. Chem. Vol. 84, 2006

Table 1 (concluded).

Time Yield
Entry Substrate Product Type of POM (min) (%)a,b,c
v HTP 40 60
OH OTs HMP 55 30
AlTP 15 80
AlMP 23 75

w OH OH HTP 120 0
HMP 120 0
No product AlTP 120 0
CH2CH3 AlMP 120 0
x HTP 120 0
HMP 120 0
CH2OH No product AlTP 120 0
AlMP 120 0
OH
y OH HTP 120 0
HMP 120 0
No product AlTP 120 0
AlMP 120 0
OH
z HTP 120 0
HMP 120 0
OH OH No product AlTP 120 0
AlMP 120 0
a
Substrate (1 mmol), p-TsCl (1.2 mmol), and POM (3 mol%) were ground together in a mortar with a pestle at room tempera-
ture for the appropriate time to form the tosylates.
b
Isolated yield.
c
Identification of the products was ascertained by NMR, IR, and mass spectrometric analysis.

Table 2. Results of the tosylation of different phenols using some heteropolyacids (polyoxometalates).
Time Yield
Entry Substrate Product Type of POM (min) (%)a,b,c
a OH OTs HTP 20 50
HMP 35 50
AlTP 10 85
AlMP 10 85

b OH OTs HTP 38 51
HMP 40 44
AlTP 5 90
AlMP 8 85

c OH OTs HTP 25 50
HMP 30 35
AlTP 5 98
CH3 CH3 AlMP 8 91

d OH OTs HTP 25 30
HMP 25 30
AlTP 8 95
AlMP 9 91
CH3 CH3
e OH OTs HTP 22 50
HMP 40 45
AlTP 10 90
H3C H3C AlMP 10 83

a
Substrate (1 mmol), p-TsCl (1.2 mmol), and POM (3 mol%) were ground together in a mortar with a pestle at room temperature
for the appropriate time to form the tosylates.
b
Isolated yield.
c
Identification of the products was ascertained by NMR, IR, and mass spectrometric analysis.

© 2006 NRC Canada

Fazaeli et al. 817

Scheme 2.

OH OTs
trace
+ 1.2 mol% p-TsCl +

3 mol % AlTP
OH OTs
Solvent-free, r.t.
(10 min) 98%

Table 3. Tosylation of cyclohexanol with p-TsCl in the presence of AlPW12O40 in various solvents.

OH OTs
3 mol % AlTP

p-TsCl
Solvent

Entry Solvent GC yield (%) after 6 min GC yield (%) after 30 min
1 CHCl3 20 50
2 CH3CN 35 65
3 CH2Cl2 10 35
4 Acetone 25 50
5 EtOH 15 35
Note: Reaction conditions: cyclohexanol (1 mmol), p-TsCl (1.2 mmol), AlPW12O40 (3 mol%), and reflux.

Table 4. Tosylation of cyclohexanol with p-TsCl in the presence of AlPMo12O40 in various solvents.
OH OTs
3 mol % AlMP

p-TsCl
Solvent
Entry Solvent GC yield (%) after 9 min GC yield (%) after 30 min
1 CHCl3 20 30
2 CH3CN 35 50
3 CH2Cl2 10 35
4 Acetone 15 35
5 EtOH 20 35
Note: Reaction conditions: cyclohexanol (1 mmol), p-TsCl (1.2 mmol), AlPMo12O40 (3 mol%), and reflux.

In the case of the aliphatic alcohols, secondary alcohols
were tosylated much faster compared with primary hydroxyl
groups (Table 1, entries k–t). Thus, a secondary alcohol can
be tosylated chemoselectively in the presence of a primary
alcohol, as previously reported in the case of CoCl2·6H2O
(8) and silica chloride (9).
The difference in reaction rates between primary and sec-
ondary alcohols, which is observed in Table 1, prompted us
to examine the chemoselective tosylation of alcohols. For
example, when a mixture of n-hexanol and cyclohexanol was
allowed to react with 0.5 equiv. p-TsCl in the presence of
these catalysts for 10 min, cyclohexanol underwent
tosylation chemoselectively in 98% yield and only a trace
amount of n-hexyl tosylate was detected (Scheme 2). These
studies clearly reveal that this methodology can be applied
for the chemoselective direct tosylation of aliphatic second-
ary alcohols in the presence of primary hydroxyl groups.
Effect of solvent
The tosylation of cyclohexanol was also conducted in dif-
ferent solvents (chloroform, acetonitrile, dichloromethane,
acetone, and ethanol). The results show that the yield of the
reaction in solutions is much less than those observed under
solvent-free conditions (Tables 3 and 4).
Effect of the catalyst
Amongst the catalysts used (H3PW12O40, H3PMo12O40,
AlPW12O40, and AlPMo12O40) in the tosylation of alcohols
© 2006 NRC Canada
818
and phenols, it was found that both AlPW12O40 and
AlPMo12O40 were effective catalysts for the tosylation of
alcohols and phenols. The results showed that in the absence
of the catalysts, the tosylation reaction did not proceed after
30 min at room temperature, but in the presence of two
heteropolyacids (AlPW12O40 and AlPMo12O40), the conver-
sion proceeded efficiently in a few minutes under similar re-
action conditions (Tables 1 and 2). Therefore, we chose
AlPW12O40 and AlPMo12O40 which are heterogeneous and
environmentally benign compounds, as catalysts for further
tosylation studies. Furthermore, the use of just 3 mol% POM
is sufficient to promote the reaction and no other additives
are required for this conversion. No improvements were ob-
served in the reaction yields by increasing the amount of
POM from 3 to 5 mol%.
Conclusions
In this study, we have introduced aluminum dodecatung-
stophosphate (AlPW12O40) and aluminium dodecamolybdo-
phosphate (AlPMo12O40) as new, highly effective,
nonhygroscopic, noncorrosive, heterogeneous, and environ-
mentally benign catalysts for the efficient tosylation of a va-
riety of alcohols and phenols in high yields. Phenols and
primary, secondary, benzylic, and allylic alcohols gave
tosylated products in good yields. In the case of aliphatic al-
cohols, secondary alcohols are transformed to the corre-
sponding tosylates chemoselectively in the presence of the
primaryhydroxy groups. The advantages of the present meth-
ods may be summarized as: high stereoselectivities, good
yields of the desired products, short reaction times, mild and
solvent-free conditions, and simple experimental procedure
and product isolation. The only disadvantage of this system
is the release of HCl as a by-product. We feel our protocol is
an attractive alternative to the existing procedures for
tosylation of alcohols and phenols.
Acknowledgment
We gratefully thank Isfahan University, Isfahan, Iran, for
financial support.
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