AlCl3.6H2O as a catalyst for simple and efficient synthesis of gem-dihydroperoxides from ketones and aldehydes using aqueous H2O2

Article abstract of DOI:10.1007/BF03246556

AlCl₃.6H₂O was explored as an efficient catalyst for the synthesis of gem-dihydroperoxides (DHPs) from ketones and aldehydes. The reactions took place within a short period of time using (30%) aqueous H ₂O₂ as a "green" oxidant in acetonitrile under neutral conditions at room temperature to afford the products in high yields.

Full text of DOI:10.1007/BF03246556

J. Iran. Chem. Soc., Vol. 8, No. 4, December 2011, pp. 1006-1013.
JOURIrNaAnLiaOnF THE
Chemical Society
AlCl3.6H2O as a Catalyst for Simple and Efficient Synthesis of gem-Dihydroperoxides
from Ketones and Aldehydes using Aqueous H2O2
D. Azarifar* and K. Khosravi
Department of Chemistry, Bu-Ali Sina University, Hamedan-65178, Islamic Republic of Iran
(Received 5 November 2010, Accepted 15 March 2011)
AlCl3.6H2O was explored as an efficient catalyst for the synthesis of gem-dihydroperoxides (DHPs) from ketones and
aldehydes. The reactions took place within a short period of time using (30%) aqueous H2O2 as a “green” oxidant in acetonitrile
under neutral conditions at room temperature to afford the products in high yields.
Keywords: gem-Dihydroperoxides, Aluminium chloride hexahydrate, AlCl3.6H2O, Ketones, Aldehydes, Aqueous H2O2
INTRODUCTION
of ketone enol ethers or α-olefines in the presence of aqueous
H2O2 [8,30,38]; (ii) treatment of ketals and ketones with H2O2
utilizing acid catalysts such as tungstic acid [14], BF3/Et2O
[16,39], and HCl [26,40], albeit 4-tert-butylcyclohexyl-1,1-
dihydroperoxide has been synthesized under neutral conditions
catalyzed by methyltrioxorhenium (MeReO3) in trifluoro-
ethanol [2], and (iii) peroxidation of ketones in an acidic
solvent, e.g. AcOH [12,41], or hydroperoxide rearrangement
of bicyclic alcohols [42]. However, these methods suffer from
certain drawbacks such as longer reaction times, use of
concentrated H2O2 and excess acid, non-recoverable catalysts,
low yields, poor selectivity of ozonolysis and the presence of
ozone-sensitive groups in the substrates.
A more general way has been reported for the synthesis of
gem-DHPs from ketones and aromatic aldehydes using
aqueous H2O2 (30%) and iodine as the catalyst in acetonitrile
[19,43]. Das et al. [18] reported an efficient method for the
synthesis of gem-DHPs from ketones and aldehydes by
aqueous H2O2 (50%) under catalytic effect of ceric ammonium
nitrate (CAN). For primary gem-DHPs this method is,
however, limited to electron-rich aromatic aldehydes. A
number of other recently reported synthetic routes to gem-
DHPs include the use of 50% H2O2 solution under acid
catalysis in THF [13], and rhenium(VII) oxide in acetonitrile
gem-Dihydroperoxides (DHPs) are stable and versatile
derivatives of ketones and aldehydes [1]. The rapidly
increasing interest in gem-dihydroperoxides stems from their
relevance to peroxidic antimalarial drugs [2-7], and the
presence of gem-peroxy linkage in gem-peroxyketals as a
salient structural feature [8-10], shared by many known
antimalarial cyclic organic peroxides [11-21]. Also, these
compounds have been used as useful precursors in the
synthesis of different peroxides including tetraoxanes [22-27],
and their analogues such as silatetraoxanes [28],
spirobisperoxyketals [29] and 1,2,4,5-tetraoxacycloalkanes
[30]. Very recently, gem-DHPs have found applications as
initiators in polymerization reactions [31,32], as reagents for
epoxidation of α,β-unsaturated ketones [33], and oxidation of
different organic molecules [34] such as sulfides [35,36].
Recently, gem-dihydroperoxides have been reported as
effective reagents for enantioselective epoxidation of 2-
substituted 1,4-naphthoquinones [37].
Synthetic methods to synthesize gem-dihydroperoxides
have been reviewed [1]. Common routes include (i) ozonolysis
*Corresponding author. E-mail: azarifar@basu.ac.ir

Azarifar & Khosravi
[20]. Moreover, silicon-supported sodium hydrogen sulfate
(ppm)): 4.45 (2H, brs, -OOH), 2.46-0.72 (16H, m, aliph-H);
13C NMR (22.5 MHz, CDCl3, δ (ppm)): 114.2, 52.0, 45.4,
39.5, 37.0, 24.6, 23.5, 21.0, 8.6; Anal. Calcd. for C10H18O4: C,
59.40; H, 8.91%. Found: C, 59.34; H, 8.87; FABMS: m/z 225
[M+Na]+.
[15], phosphomolybdic acid [44], and camphorsulfonic acid
[17], have been reported for the synthesis of primary gem-
DHPs from ketones and aldehydes.
EXPERIMENTAL
3-Bromo-2,2-dihydroperoxy-1,7,7-trimethyl-bicyclo
[2.2.1]heptane (2h). Colorless solid; m.p.: 68-70 ºC; IR (KBr,
cm-1): 3410 (O-H stretching of hydroperoxy groups), 2956,
2853, 1618, 1478, 1384, 1316, 1205, 1034, 910, 768; 1H NMR
(FT-90 MHz, CDCl3, δ (ppm)): 4.56 (2H, brs, -OOH), 2.27-
0.91 (15H, m, aliph-H); 13C NMR (22.5 MHz, CDCl3, δ
(ppm)): 120.3, 54.0, 46.8, 40.0, 38.3, 26.6, 24.7, 22.4, 9.6;
Anal. Calcd. for C10H17BrO4: C, 42.70; H, 6.05%. Found: C,
42.63; H, 5.97%; FABMS: m/z: 304 [M+Na]+.
Solvents, reagents, and chemical materials were obtained
from Aldrich and Merck chemical companies and purified
prior to use. Melting points were determined in open capillary
tubes in a Stuart SMP3 apparatus and uncorrected. Nuclear
magnetic resonance spectra were recorded on JEOL FX 90Q
using tetramethylsilane (TMS) as an internal standard. Infrared
spectra were recorded on a PerkinElmer GX FT IR
spectrometer (KBr pellets).
Caution: Although we did not encounter any problem with
these reactions, peroxidic compounds are potentially explosive
and should be handled with some caution; all reactions should
be carried out behind a safety shield inside a fume hood and
transition metal salts or heating should be avoided.
Methyl-(naphthalen-1-yl)-1,1-dihydroperoxide
(2k).
Colorless oil; IR (KBr, cm-1): 3324, 3052 (O-H stretching of
hydroperoxy groups), 2922, 2853, 1594, 1573, 1508, 1461,
1
1356, 1279, 1240, 1192, 1128, 941, 863, 802, 775, 591; H
NMR (FT-90 MHz, CDCl3, δ (ppm)): 8.83-8.75 (2H, brs,
-OOH), 8.10-7.20 (7H, m, Ar-H), 2.66 (3H, s, CH3); 13C NMR
(22.5 MHz, CDCl3, δ (ppm)): 136.0, 134.4, 131.1, 129.9,
127.8, 126.6, 125.5, 123.0, 107.0, 20.5; Anal. Calcd. for
C12H12O4: C, 65.45; H, 5.45%. Found: C, 65.42; H, 5.40%;
FABMS: m/z 243 [M+Na]+.
General Procedure for the Synthesis of gem-
Dihydroperoxides 2
A mixture of carbonyl substrates 1 or 3 (1 mmol), 30%
aqueous H2O2 (3 ml) and AlCl3.6H2O (0.1 mmol) in MeCN (4
ml) was stirred at room temperature for 3-10 h (Table 1). After
completion of the reaction (TLC), the mixture was diluted
with water (5 ml) and extracted with EtOAc (3 × 5 ml). The
combined organic layer was washed with saturated aqueous
sodium bicarbonate solution (3 ml), dried over anhydrous
Na2SO4 and concentrated in vacuo. The residue was purified
by silica-packed column chromatography (hexane-EtOAc) to
Benzoyl-phenyl-1,1-dihydroperoxide (2n). Colorless
solid; m.p.: 118-120 ºC; IR (KBr, cm-1): 3427, 3071 (O-H
stretching of hydroperoxy groups), 2841, 2699, 2559, 1688
(C=O streching), 1603, 1583, 1454 (C=C stretching of
aromatic ring), 1384, 1292, 1128, 1072, 1026, 934, 809, 700,
1
667; H NMR (FT-90 MHz, CDCl3, δ (ppm)): 8.81 (2H, brs,
-OOH), 8.10-7.95 (4H, m, Ar-H), 7.50-7.10 (6H, m, Ar-H);
Anal. Calcd. for C14H12O5: C, 64.61; H, 4.61%. Found: C,
64.54; H, 4.57%; FABMS: m/z 283 [M+Na]+.
afford pure gem-dihydroperoxides
2
(or hydroxyl-
hydroperoxides 4) (Table 1). The products were characterized
on the basis of their physical properties and spectral (1H, 13C
NMR and IR) data which were in accord with those reported
in the literature.
(4-Bromophenyl)methylene-1,1-dihydroperoxide (4q).
Colorless solid; m.p.: 88-90 ºC; IR (KBr, cm-1): 3426, 3085
(O-H stretching of hydroperoxy groups), 2909, 1608, 1528,
1411 (C=C stretching of aromatic ring), 1353, 1236, 1195,
1
1083, 973, 856, 828, 753, 706, 601; H NMR (FT-90 MHz,
Spectral Data of New Compounds
CDCl3, δ (ppm)): 9.96 (2H, brs, -OOH), 7.90-7.00 (4H, m, Ar-
H), 6.26 (1H, s, CH); 13C NMR (22.5 MHz, CDCl3, δ (ppm)):
141.0, 132.5, 130.5, 120.0, 111.0; Anal. Calcd. for C7H7BrO4:
C, 35.74; H, 2.97%. Found: C, 35.72; H, 2.94%; FABMS: m/z
258 [M+Na]+.
2,2-Dihydroperoxy-1,7,7-trimethyl-bicyclo[2.2.1]
heptane (2g). Colorless oil; IR (KBr, cm-1): 3473 (O-H
stretching of hydroperoxy groups), 2973, 2853, 1589, 1448,
1
1385, 1268, 1146, 1017; H NMR (FT-90 MHz, CDCl3, δ
1007

AlCl3.6H2O as a Catalyst for Simple and Efficient Synthesis of gem-Dihydroperoxides
Table 1. Effects of Catalyst and Solvent in the Synthesis of gem-DHPsa
Entry
Ketone 1/Aldehyde 3
Catalyst
Solvent
Time (h)
Yield (%)b
1
2
3
4
5
6
7
8
3-Pentanone
3-Pentanone
3-Pentanone
3-Pentanone
3-Pentanone
3-Pentanone
3-Pentanone
3-Pentanone
Cyclohexanone
Cyclohexanone
Cyclohexanone
Cyclohexanone
Cyclohexanone
Acetophenone
Acetophenone
Acetophenone
Acetophenone
Acetophenone
Benzaldehyde
Benzaldehyde
Benzaldehyde
Benzaldehyde
Benzaldehyde
AlCl3.6H2O
AlCl3.6H2O
AlCl3.6H2O
AlCl3.6H2O
SbCl3
CH3CN
CH2Cl2
Et2O
3
5
8
5
8
10
8
10
3
7
96
82
60
87
48
45
75
Trace
98
55
50
70
Trace
56
23
15
28
0
AcOEt
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CeO2
CrCl3.6H2O
KF-Al2O3
AlCl3.6H2O
SbCl3
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
CeO2
8
6
CrCl3.6H2O
KF-Al2O3
AlCl3.6H2O
SbCl3
10
8
12
12
10
20
8
15
15
12
20
CeO2
CrCl3.6H2O
KF-Al2O3
AlCl3.6H2O
SbCl3
CeO2
CrCl3.6H2O
KF-Al2O3
67
32
15
22
0
aConditions: ketone and aldehyde (1 mmol), solvent (4 ml), catalyst (0.1 mmol), 30% aq.
H2O2 (3 ml), reactions are carried out at rt. bIsolated yields.
4.05 (3H, s, OCH3); 13C NMR (22.5 MHz, CDCl3, δ (ppm)):
157.4, 139.1, 128.5, 123.0, 118.5, 102.0, 57.5; Anal. Calcd. for
C8H10O5: C, 51.61; H, 5.37%. Found: C, 51.57; H, 5.34%;
FABMS: m/z 209 [M+Na]+.
(4-Flourophenyl)methylene-1,1-dihydroperoxide (4s).
Colorless solid; m.p.: 110-112 ºC; IR (KBr, cm-1): 3464, 3082
(O-H stretching of hydroperoxy groups), 2905, 1625, 1601,
1564, 1453 (C=C stretching of aromatic ring), 1353, 1303,
1
1071, 1025, 844, 720, 685; H NMR (FT-90 MHz, CDCl3, δ
(ppm)): 9.21 (2H, brs, -OOH), 8.14-7.14 (4H, m, Ar-H), 6.14
(1H, s, CH); 13C NMR (22.5 MHz, CDCl3, δ (ppm)): 161.62,
137.0, 128.5, 118.5, 112.0; Anal. Calcd. for C7H7FO4: C,
48.27; H, 4.02%. Found: C, 48.23; H, 3.97%; FABMS: m/z
197 [M+Na]+.
(2-Methoxyphenyl)methylene-1,1-dihydroperoxide
(4u). Colorless oil; IR (KBr, cm-1): 3226, 3085 (O-H
stretching of hydroperoxy groups), 2853, 1647, 1603, 1493,
1465 (C=C stretching of aromatic ring), 1372, 1245, 1177,
1017, 844, 758; 1H NMR (FT-90 MHz, CDCl3, δ (ppm)): 9.35
(2H, brs, -OOH), 8.18-6.84 (4H, m, Ar-H), 6.04 (1H, s, CH),
RESULTS AND DISSCUTION
In our ongoing research for making developments in the
synthesis of gem-DHPs [45], and their applications in various
transformations [36,46,47], herein, we introduce AlCl3.6H2O
as another new and highly efficient catalyst to effect the
synthesis of gem-DHPs from ketones and aldehydes
employing aqueous H2O2 (30%) at room temperature.
The effects of catalysts and solvents were investigated in
order to obtain suitable reaction conditions in terms of yield
and reaction time for the conversion of the ketones and
1008

Azarifar & Khosravi
aldehydes into their corresponding DHPs. Various catalysts
and solvents were examined using 3-pentanone,
cyclohexanone, acetophenone, and benzaldehyde as test
compounds in aqueous H2O2 (30%) at room temperature. The
obtained results are summarized in Table 1. As could be seen
in this table, the best results emerged when AlCl3.6H2O (10
mol%) was employed as a catalyst using MeCN as the solvent
of choice. It appears that, the solvent polarity plays important
role in the synthesis of DHPs. The other catalysts such as
SbCl3, CeO2 and CrCl3.6H2O resulted in moderate to low
yields while KF-Al2O3 was found quite unsuitable for this
synthesis.
Scheme 1
To develop the scope of the reaction, we determined to
extend this reaction to a variety of other cyclic and acyclic
aliphatic and aromatic ketones 1a-n and aldehydes 1o-v under
the optimized conditions (rt, 0.1 mol% catalyst, in MeCN)
(Scheme 1). The experimental results are summarized in Table
2. The gem-dihydroperoxides 2a-k corresponding to the
a,b
Table 2. Synthesis of gem-Dihydroperoxides with AlCl3.6H2O (cat.)/30% aq. H2O2
Entry
Ketone 1/Aldehyde 3
Productc 2 or 4
Time (h) Yield (%)d
Ref.
[43]
O
HOO OOH
4 (5)
3 (4)
97 (95)
96 (93)
a
HOO OOH
O
[18]
b
O
HOO OOH
OOH OOH
3.5 (4)
3 (5)
95 (92)
98 (90)
[18]
[15]
c
O
d
O
O
OOH
OOH
HOO
HOO
3 (4)
97 (94)
[44]
e
3 (4)
4
93 (90)
68
[20]
new
f
g
OOH
OOH
O
5
58
new
[18]
h
i
Br
Br
OOH
OOH
O
O
OOH
HOO
8 (11)
56 (45)
1009

AlCl3.6H2O as a Catalyst for Simple and Efficient Synthesis of gem-Dihydroperoxides
Table 2. Continued
O
OOH
HOO
8 (11)
56 (45)
[18]
i
O
O
OOH
HOO
7.5 (9)
4
82 (62)
95
[19]
new
j
MeO
MeO
OOH
OOH
k
O
-
12
10
-
-
l
O
O
Me
OOH
Me
87
[36]
m
HOO
O
O
O
OOH
HOO
12
75
new
n
O
O
OOH
HOO
CHO
CHO
8 (12)
67 (50)
64 (52)
[18]
[43]
o
OOH
OOH
HOO
HOO
10 (12)
p
CHO
9
85
new
q
Br
Br
HOO
HOO
OOH
OOH
CHO
CHO
8 (10)
11
80 (75)
84
[43]
new
r
Cl
Cl
F
s
F
HOO
OOH
CHO
8.5 (10)
78 (60)
[44]
t
MeO
OMe
1010

Azarifar & Khosravi
Table 2. Continued
HOO
OOH
OMe
CHO
OMe
10 (10)
10 (11)
75 (60)
82 (70)
new
[45]
u
HOO
OOH
CHO
v
NC
CN
O
HO OOH
4 (5)
5 (6)
93 (90)
95 (88)
[48]
[48]
w
x
H
H
O
HO OOH
H
H
aConditions: ketone and aldehyde (1 mmol), acetonitrile (4 ml), AlCl3.6H2O (0.1 mmol), 30% aq. H2O2 (3
ml), reactions are carried out at rt. bThe yields and reaction times obtained under similar conditions using
SnCl2.3H2O catalyst [45] are quoted in the parentheses. cThe structures of the products were established
from their physical properties and spectral (1H, 13C NMR and MS) analysis and compared with the
literature. dIsolated yield.
ketones afforded high to excellent yields (56-98%) within 3-8
h (Table 2). However, under the same reaction condition, no
conversion to gem-DHP was observed for benzophenone 1k
and it was recovered almost intact after 12 h. This, possibly,
can be accounted for by the strong resonance stabilization and
steric effects exerted by the presence of two phenyl groups. In
this reaction, acetylacetone 1m gave trans-3,5-dihydroperoxy-
3,5-dimethyl-1,2-dioxolane (87%) [36], while only one of the
two carbonyl groups present in dibenzoyl 1n underwent
conversion to corresponding dihydroperoxide 2n (75%).
Similarly, the aromatic aldehydes 1o-v were converted to their
corresponding gem-DHPs 2o-v in (64-85%) yield (Table 1).
As we previously noted [45], and is also reported by
Rieche [48] and others [49], this method proved unsuitable for
converting aliphatic aldehydes such as octanal 3w and
hydrocinnamaldehyde 3x into their corresponding gem-DHPs
under the same reaction conditions which transferred
benzaldehyde into gem-DHP. Instead, these compounds were
both converted into their corresponding hydroxyl-
hydroperoxides 4w and 4x respectively (Scheme 2, Table 1),
Scheme 2
that is, the addition of just one molecule of hydrogen peroxide
to the carbonyl group has occurred.
As shown in Table 2, AlCl3.6H2O appears to catalyze these
reactions more efficiently to furnish the respective gem-DHPs
in considerably higher yields and shorter reaction times than
SnCl2.3H2O catalyst reported in our previous work [45].
Moreover, AlCl3.6H2O is believed to be environmentally more
friendly and benign in comparison with SnCl2.3H2O and many
other previously reported catalysts.
CONCLUSIONS
In summary, a new, efficient and cheaply available catalyst
AlCl3.6H2O has been explored to effect the synthesis of gem-
1011

AlCl3.6H2O as a Catalyst for Simple and Efficient Synthesis of gem-Dihydroperoxides
dihydroperoxides from aliphatic and aromatic ketones and
[14] C.W. Jefford, W.Li, A. Jaber, J. Boukouvalas, Synth.
aldehydes using aqueous H2O2 (30%) in acetonitrile at room
temperature. The attractive features of this new approach are:
the readily available and non-toxic catalyst, the high yields,
mild reaction condition and the operational simplicity of the
procedure.
Cmmun. 20 (1990) 2589.
[15] B. Das, B. Veeranjaneyulu, M. Krishnaiah, P.
Balasubramanyam, J. Mol. Catal. A: Chem. 284 (2008)
116.
[16] A.O. Terent’ev, A.V. Kutkin, M.M. Platonov, Y.N.
Ogibin, G.I. Nikishin, Tetrahedron Lett. 44 (2003)
7359.
[17] A. Bunge, H.J. Hamann, J. Liebscher, Tetrahedron Lett.
50 (2009) 524.
[18] B. Das, M. Krishnaiah, B. Veeranjaneyulu, B.
Ravikanth, Tetrahedron Lett. 48 (2007) 6286.
[19] K. Zmitek, M. Zupan, S. Stavber, J. Iskra, Org. Lett. 8
(2006) 2491.
ACKNOWLEDGEMENTS
We wish to thank the Research Council of Bu-Ali Sina
University, Hamedan, Iran, for their financial support to carry
out this research.
REFERENCES
[20] P. Ghorai, P.H. Dussault, Org. Lett. 10 (2008) 4577.
[21] P. Ghorai, P.H. Dussault, Org. Lett. 11 (2009) 213.
[22] K. Zmitek, S. Stavber, M. Zupan, D. Bonnet-Delpon, J.
Iskra, Tetrahedron 62 (2006) 1479.
[23] A.O. Terent’ev, A.V. Kutkin, Z.A. Starikova, M.Y.
Antipia, Y.N. Ogibin, G.I. Nikishina, Synthesis (2004)
2356.
[24] Y.X. Dong, J.L. Vennerstrom, J. Org. Chem. 63 (1998)
8582.
[25] K. Zmitek, S. Stavber, M. Zupan, D. Bonnet-Delpon, S.
Charneau, P. Grellier, J. Skra, J. Bioorg. Med. Chem.
14 (2006) 7790.
[26] D. Opsenica, G. Pocsfalvi, Z. Juranic, B. Tinant, J.P.
Declercq, D.E. Kyle, W.K. Milhous, B.A. Solaja, J.
Med. Chem. 43 (2000) 3274.
[27] Y. Dong, Mini-Rev. Med. Chem. 2 (2002) 113.
[28] A.O. Terent’ev, M.M. Platonov, A.I. Tursina, V.V.
Chemyshev, G.I. Nikishin, J. Org. Chem. 73 (2008)
3169.
[1]
[2]
[3]
[4]
[5]
[6]
K. Zmitek, M. Zupan, J. Iskra, Org. Biomol. Chem. 5
(2007) 3895.
J. Iskra, D. Bonnet-Delpon, J.P. Begue, Tetrahedron
Lett. 44 (2003) 6309.
Y.Q. Tang, Y.X. Dong, J.L. Vennerstrom, Med. Res.
Rev. 24 (2004) 425.
A. Masuyama, J.M. Wu, M. Nojima, H.S. Kim, Y.
Wataya, Mini-Rev. Med. Chem. 5 (2005) 1035.
K. Borstnik, I.H. Mpaik, T.A. Shapiro, G.H. Posner,
Int. J. Parasitol. 32 (2002) 1661.
J. Wiesner, R. Ortmann, H. Jomaa, M. Schlitzer,
Angew. Chem., Int. Ed. 42 (2003) 5274.
[7] Y. Hamada, H. Tokuhara, A. Masuyama, M. Nojima,
H.S. Kim, K. Ono, N. Ogura, Y. Wataya, J. Med.
Chem. 45 (2002) 1374.
[8]
H.S. Kim, K. Tsuchiya, Y. Shibata, Y. Wataya, Y.
Ushigoe, A. Masuyama, M. Nojima, K.J. McCullough,
J. Chem., Perkin Trans. 1 (1867) 1999.
[9]
K. Tsuchiya, Y. Hamada, A. Masuyama, M. Nojima,
Tetrahedron Lett. 40 (1999) 4077.
[29] P. Ghorai, P.H. Dussault, C. Hu, Org. Lett. 10 (2008)
2401.
[10] Y. Dong, H. Matile, J. Chollet, R. Kaminski, J.K.
Wood, J.L. Vennerstrom, J. Med. Chem. 42 (1999)
1477.
[11] T. Ledaal, T. Solbjor, Acta Chem. Scand. 21 (1967)
1658.
[12] A. Ramirez, K.A. Woerpel, Org. Lett. 7 (2005) 4617.
[13] A.O. Terent’ev, M.M. Platonov, Y.N. Ogibin, G.I.
Nikishin, Synth. Commun. 37 (2007) 1281.
[30] H.S. Kim, Y. Nagai, K. Ono, K. Begum, Y. Wataya, Y.
Hamada, K. Tsuchiya, A. Masuyama, M. Nojima, K.J.
McCullough, J. Med. Chem. 44 (2001) 2357.
[31] W. Adam (Ed.), Peroxide Chemistry, Mechanistic and
Preparative Aspects of Oxygen Transfer, Wiley-VCH,
Weinheim, Germany, 2000.
[32] W. Ando (Ed.), Organic Peroxides, John Wiley & Sons,
Chichester, UK, 1992.
1012

Azarifar & Khosravi
[33] K. Jakka, J. Liu, C.G. Zhao, Tetrahedron Lett. 48
688.
(2007) 1395.
[41] T. Ledaal, T. Solbjor, Acta Chem. Scand. 21 (1967)
1658.
[42] H.J. Hamann, J. Liebscher, Synlett (2001) 96.
[43] K. Zmitek, M. Zupan, S. Stavber, J. Iskra, J. Org.
Chem. 72 (2007) 6534.
[44] Y. Li, H.-D. Hao, Q. Zhang, Y. Wu, Org. Lett. 11
(2009) 1615.
[45] D. Azarifar, K. Khosravi, F. Soleimanei, Synthesis
(2009) 2553.
[34] H. Saneyyoshi, K. Miyata, K. Seio, M. Sekine,
Tetrahedron Lett. 47 (2006) 8945.
[35] J. Jon Paul Selvam, V. Suresh, K. Rajesh, D. Chanti
Babu, N. Suryakiran, Y. Venkateswarlu, Tetrahedron
Lett. 49 (2008) 3463.
[36] D. Azarifar, K. Khosravi, Eur. J. Chem. 1 (2010) 15.
[37] A. Bunge, H.J. Hamann, E. McCalmont, J. Leibscher,
Tetrahedron Lett. 50 (2009) 4629.
[38] T. Ito, T. Tokuyasu, A. Masuyama, M. Nojima, K.J.
McCullough, Tetrahedron 59 (2003) 525.
[39] A.O. Terent’ev, A.V. Kutkin, N.A. Troizky, Y.N.
Ogibin, G.I. Nikishin, Synthesis (2005) 2215.
[40] N.M. Todorovic, M. Stefanovic, B. Tinant, J.P.
Declercq, M.T. Malker, B.A. Solaja, Steroids 61 (1996)
[46] D. Azarifar, K. Khosravi, Synlett (2010) 2755.
[47] D. Azarifar, K. Khosravi, Z. Najminejad, K. Soleimani,
Heterocycles 81 (2010) 2855.
[48] A. Rieche, Chem. Ber. 64 (1931) 2328.
[49] R.A. McClelland, M. Coe, J. Am. Chem. Soc. 105
(1983) 2718.
1013