See discussions, stats, and author profiles for this publication at: https://www.researchgate.

net/publication/254237362

NH4H2PO4/SiO2: A recyclable, efficient heterogeneous catalyst for crossed

aldol condensation reaction

Article  in  Green Chemistry Letters and Reviews · January 2011

DOI: 10.1080/17518253.2011.617317

CITATIONS READS
9 202

4 authors, including:

Gholam Hossein Hossein Mahdavinia Shahnaz Rostamizadeh

Islamic Azad University Khaje Nasir Toosi University of Technology
59 PUBLICATIONS   1,065 CITATIONS    82 PUBLICATIONS   1,296 CITATIONS   

SEE PROFILE SEE PROFILE

Ali Mohammad Amani

Shiraz University of Medical Sciences
95 PUBLICATIONS   1,598 CITATIONS   

SEE PROFILE

Some of the authors of this publication are also working on these related projects:

Synthesis of a novel ZnO nanoplates supported hydrazone-based palladacycle as an effective and recyclable heterogeneous catalyst for the Mizoroki–Heck cross-coupling
reaction View project

Investigating Drug Delivery Methods View project

All content following this page was uploaded by Ali Mohammad Amani on 24 April 2017.

The user has requested enhancement of the downloaded file.

This article was downloaded by: [Dalhousie University]
On: 02 January 2013, At: 03:39
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House,
37-41 Mortimer Street, London W1T 3JH, UK

Green Chemistry Letters and Reviews

Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/tgcl20

NH4H2PO4/SiO2: a recyclable, efficient heterogeneous

catalyst for crossed aldol condensation reaction
a b a
Gholam Hossein Mahdavinia , Shahnaz Rostamizadeh , Ali Mohammad Amani & Maryam
c
Mirzazadeh
a
Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran
b
Department of Chemistry, K.N. Toosi University of Technology, P.O. Box 15875-4416,
Tehran, Iran
c
Department of Chemistry, Firoozabad Branch, Islamic Azad University, Fars, Iran
Version of record first published: 03 Aug 2012.

To cite this article: Gholam Hossein Mahdavinia , Shahnaz Rostamizadeh , Ali Mohammad Amani & Maryam Mirzazadeh
(2012): NH4H2PO4/SiO2: a recyclable, efficient heterogeneous catalyst for crossed aldol condensation reaction, Green
Chemistry Letters and Reviews, 5:3, 255-281

To link to this article: http://dx.doi.org/10.1080/17518253.2011.617317

PLEASE SCROLL DOWN FOR ARTICLE

For full terms and conditions of use, see: http://www.tandfonline.com/page/terms-and-conditions

esp. Part II. Intellectual property and access and license types, § 11. (c) Open Access Content

The use of Taylor & Francis Open articles and Taylor & Francis Open Select articles for commercial
purposes is strictly prohibited.

The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses should
be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims,
proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or indirectly in
connection with or arising out of the use of this material.
 Green Chemistry Letters and Reviews
Vol. 5, No. 3, September 2012, 255
281

RESEARCH LETTER
NH4H2PO4/SiO2: a recyclable, efficient heterogeneous catalyst for crossed aldol condensation
reaction
Gholam Hossein Mahdaviniaa*, Shahnaz Rostamizadehb, Ali Mohammad Amania and Maryam Mirzazadehc

a
Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran; bDepartment of Chemistry, K.N.
Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran; cDepartment of Chemistry, Firoozabad Branch, Islamic
Azad University, Fars, Iran
(Received 3 April 2011; final version received 13 May 2011)

Crossed aldol condensation of aromatic aldehydes with cyclic ketones in the presence of catalytic amount of
NH4H2PO4/SiO2 (as a safe, green, and cheap heterogeneous catalyst) under solvent-free condition afforded a,á-
Downloaded by [Dalhousie University] at 03:39 02 January 2013

bis(substituted-benzylidene) cycloalkanones in high yields. This method is general with respect to all types of
aromatic aldehydes and is an eco-friendly procedure. And the catalyst is easily prepared, stable, reusable, and
efficient under the reaction conditions.
Keywords: aromatic aldehydes; a,á-Bis(substituted-benzylidene) cycloalkanones; crossed aldol condensa-
tion; cyclic ketones; NH4H2PO4/SiO2

Introduction (29), BMPTO(bis(p-ethoxyphenyl)telluroxide) (30),

Cross-aldol condensation of aromatic aldehydes with
cyclic ketones is an important protocol for the
synthesis of a,á-bis(substituted-benzylidene)cycloalk-
anones, which are very important precursors to
potentially bioactive pyrimidine derivates (1), inter-
mediates for agrochemical, pharmaceuticals and per-
fumes (2), new organic material for nonlinear optical
applications (3), cytotoxic analogous (4), bis-spiro-
pyrrolidines (5), and the units of liquid crystalline
polymers (6). Usually, this condensation process is
catalyzed by strong acid or base, however, suffers
from side reactions (such as self-condensation of
ketones and aldehydes) giving the corresponding
products in low yields (7,8). Therefore, numerous
studies in the literature to improve the performance
of the reaction have existed; the main progress was
the following: (1) The aldol reaction was catalyzed by
organometallic complexes but the yields were not
satisfactory (9) or required long reaction time (10), (2)
Lewis acid such as RuCl3 (11), SmI3 (12), BF3Et2O
(13,14), FeCl3 6H2O (15), Mg(HSO4)2 (16), KHSO4
(17), Yb(OTf)3 (18), Cu(II) trifluoroacetate (19),
InCl3 4H2O (20), LiClO4 (21), NKC-9 (polymer-
supported sulfonic acid) (22), SiO2
Pr
SO3H (23)
were used to promote the aldol reaction, and (3) I2
(24), TMSCl/NaI (25), LiOH (26), KF/Al2O3 (27),
[(Me3Si)2N]3Ln(m-Cl)Li(THF)3 (28), Silica Chloride
TCT(2,4,6-trichloro[1,3,5]triazine) (31) NaOH in mi-
cellar medium (32), KOH (33), Na-HAP (34), and
animal bone meal (35) were also found to accelerate
this type of reaction. However, the use of toxic
reagents, long reaction time, low yields, formation
of a mixture of products, and tedious separation
procedures is among the drawbacks of the reported
methods. It is therefore important to find a more
convenient method for the preparation of these
compounds.
Silica gel and silica-supported reagents has been
used as catalyst in organic synthesis because it is
easily available, inexpensive, and nontoxic. Use of
such a heterogeneous catalyst benefits several poten-
tial catalyst reuses and waste production minimiza-
tions (36
38).
Among of many silica-supported catalysts em-
ployed, NH4H2PO4/SiO2, one of the solid supported
catalysts has already been prepared by our research
group (39) and approved to be a potential green
catalyst with several advantages such as low toxicity,
low cost, ease of handling, and high catalytic activity.
In continuation of our work to develop new and eco-
friendly synthetic methodologies, herein we report a
novel, green, facile, and efficient one-pot method for
the synthesis of a,á-bis(substituted-benzylidene) cy-
cloalkanones catalyzed by NH4H2PO4/SiO2 under
solvent-free condition (Scheme 1).

*Corresponding author. Email: hmahdavinia@gmail.com

ISSN 1751-8253 print/ISSN 1751-7192 online

# 2012 Gholam Hossein Mahdavinia, Shahnaz Rostamizadeh, Ali Mohammad Amani and Maryam Mirzazadeh
http://dx.doi.org/10.1080/17518253.2011.617317
http://www.tandfonline.com
 256 G.H. Mahdavinia et al.

O O Table 1. Reaction of benzaldehyde and cyclohexanone

NH4H2PO4/SiO2 Ar under solvent-free conditions.
ArCHO + Ar
Z Solvent free Z NH4H2PO4/ Temperature Time Yield
Entry SiO2 (g) (8C) (min) (%)
Z=CH2, CH2CH2, CH(Me)CH2

1 2
1 0.00 80
110 180

3
2 0.05 80 150 Trace
Scheme 1. 3 0.05 80 120 Trace
4 0.05 110 60 10
Results and discussion 5 0.1 80 30 10
6 0.1 110 30 20
Initially, the reaction was performed by reacting 7 0.15 80 30 85
cyclohexanone (1 equiv) and benzaldehyde (2 equiv) 8 0.15 110 20 90
in the presence of 0.05 g of NH4H2PO4/SiO2 as a 9 0.15 110 15 90
catalyst under solvent-free condition at 808C. Under
these conditions, only a trace amount of product was mation was investigated by the use of 0.05
0.15 g. of
obtained after 150 min. The conditions for this catalyst. Under these conditions, the yields were in a
Downloaded by [Dalhousie University] at 03:39 02 January 2013

transformation were optimized and the results are
shown in Table 1. No product was obtained in the
absence of the catalyst (Table 1, entry 1) even when
the reaction time was extended to 180 min., thus
demonstrating the importance of NH4H2PO4/SiO2.
The amount of the catalyst required for the transfor-
range of 10
90% (Table 1). The use of 0.15 g of
NH4H2PO4/SiO2 gave the best result (Table 1, entry
9). The reaction worked well with electron-withdraw-
ing (NO2, Cl) as well as electron-donating (Me, MeO,
N(CH3)2) groups, giving various a,á-bis(substituted-
benzylidene) cycloalkanones in 85
94% yields. As it

Table 2. Preparation of a,á-bis(substituted benzylidene)cycloalkanones catalyzed by NH4H2PO4/SiO2 at 1108C under

solvent-free conditions.

Yield
Entry Ar Z Time (min) Product (%) Mp (8C) Lit. Mp (8C)

1 C6H5 CH2 15 3a 90 188
189 188
190 (18)

2 p-MeC6H4 CH2 10 3b 85 242
243 243
244 (18)
3 p-MeOC6H4 CH2 8 3c 90 211
212 211
212 (18)
4 p-ClC6H4 CH2 10 3d 92 228
229 228
229 (18)
5 p-NO2C6H4 CH2 15 3e 90 229
230 229
231 (18)
6 p-Me2NC6H4 CH2 15 3f 85 271
273 270
273 (18)
7 C6H5CH CH CH2 20 3g 85 222
223 215
216 (18)
8 o-ClC6H4 CH2 12 3h 85 154
156 152
153 (10)
9 C6H5 CH2CH2 10 3i 90 116
117 117
118 (18)
10 p-MeC6H4 CH2CH2 10 3j 92 170
171 164
165 (18)
11 p-MeOC6H4 CH2CH2 10 3k 90 162
164 161
163 (18)
12 p-ClC6H4 CH2CH2 12 3l 90 146
148 147
148 (11)
13 p-NO2C6H4 CH2CH2 10 3m 94 160
162 161
162 (18)
14 p-Me2NC6H4 CH2CH2 20 3n 92 250
252 250
252 (18)
15 C6H5CH CH CH2CH2 20 3o 90 179
180 177
178 (18)
16 o-ClC6H4 CH2CH2 20 3p 85 103
104 102
104 (31)
17 C6H5 CH(Me)CH2 15 3q 90 99
100 97
99 (31)
18 p-MeC6H4 CH(Me)CH2 15 3r 90 125
127 125
127 (31)
19 p-MeOC6H4 CH(Me)CH2 15 3s 92 137
139 137
139 (31)
20 p-ClC6H4 CH(Me)CH2 15 3t 94 158
160 156
160 (31)

O O
H2O
SiO2 OH + NH4 O P OH SiO2 O P OH + NH3
OH OH

Scheme 2.
 Green Chemistry Letters and Reviews 257
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Figure 1. (A) Infrared spectra of SiO2 (Silica gel only). (B) Infrared spectra of catalyst (NH4H2PO4/SiO2) before using it. (C)
Infrared spectra of catalyst (NH4H2PO4/SiO2) after using it.
 258 G.H. Mahdavinia et al.
Table 3. The recycling of NH4H2PO4/SiO2 in synthesis of
3d.
Entry Time (min) Yield (%)
1 40 92
2 40 92
3 60 90
4 60 90
5 90 85
is shown in Table 2, the method is general and
encompasses a variety of aromatic aldehydes with
excellent yields. The reaction worked with aliphatic
aldehydes but did not react well.
Experimental
Downloaded by [Dalhousie University] at 03:39 02 January 2013
Preparation of NH4H2PO4/SiO2
The catalyst was prepared by mixing silica gel (1.5 g,
Merck grade 60, 230
400 mesh) with a solution of
NH4H2PO4 (0.6 g, 5 mmol) in distilled water (10 mL).
The resulting mixture was stirred for 30 min to absorb
NH4H2PO4 on surface of silica gel (Scheme 2). After
removal of water in a rotary evaporator, the solid
powder was dried at 1208C for 2
3 h under reduced
pressure. The drying temperature was maintained
below the decomposition temperature of the salt.
Infrared spectras of silica gel and catalyst, before
and after using it, were shown in Figure 1. Frequency
comparison of IR spectras show the appearance of
absorption in region 1400 cm 1. This absorption is
due to the PO stretching vibrations of
OPO3H2
groups presence that was shown in Scheme 2.
Synthesis of a,á-bis(substituted-benzylidene)
cycloalkanones: general procedure
A mixture of aromatic aldehyde (2 mmol), cyclic
ketones (1 mmol), and NH4H2PO4/SiO2 (0.15 g) was
stirred for 2 min at room temperature and then the
temperature was raised to 1108C and maintained for
the appropriate time (Table 2). After completion of
the reaction (monitored by TLC), the reaction
mixture was diluted with hot ethanol and the catalyst
was filtrated off, the residue was kept at room
temperature and the resulting crystal product was
collected by filtration and washed with ethanol. The
product was found to be pure and no further
purification was necessary.
The 1H-NMR data of some compounds are given
below:
Compound 3q. 1H-NMR (300 MHz, CDCl3): d
7.81 (dbr, 2H, J 1.6 Hz), 7.32
7.49 (10H, Ar), 3.10
(ddbr, 2H, J  3.5, 15.8 Hz), 2.52 (ddd, 2H, J 2.6,
11.4, 15.8 Hz), 1.89 (m, 1H), and 1.10 (d, 3H, J 6 Hz).
Compound 3r. 1H-NMR (300 MHz, CDCl3): d
7.79 (dbr, 2H, J 1.6 Hz), 7.21
7.39 (8H, Ar), 3.10
(ddbr, 2H, J 3.5, 15.7 Hz), 2.50 (ddd, 2H, J 2.4,
11.3, 15.7 Hz), 2.39 (s, 3H), 1.87 (m, 1H), and 1.08 (d,
3H, J  6.3 Hz).
Compound 3s.1H-NMR (300 MHz, CDCl3): d
7.77 (dbr, 2H, J 1.6 Hz), 6.92
7.47 (8H, Ar), 3.85
(s, 3H), 3.06 (ddbr, 2H, J 3.5, 15.7 Hz), 2.50 (ddd,
2H, J 2.4, 11.3, 15.7 Hz), 1.88 (m, 1H), and 1.10 (d,
3H, J  6.5 Hz).
Compound 3t. 1H-NMR (300 MHz, CDCl3): d
7.73 (dbr, 2H, J  1.6 Hz), 7.38 (8H, Ar), 2.99 (ddbr,
2H, J  3.5, 15.7 Hz), 2.48 (ddd, 2H, J 2.6, 11.2,
15.7 Hz), 1.88 (m, 1H), and 1.08 (d, 3H, J  6.5 Hz).
Reusability of catalyst
Next, we investigated the reusability and recycling of
NH4H2PO4/SiO2. A mixture of p-cholorobenzalde-
hyde, cyclopentanone, and H4H2PO4/SiO2 was stirred
at 1108C in solvent-free condition. After completion
of the reaction, the reaction mixture was diluted with
hot ethanol and the catalyst was separated by simple
filtration and recovered NH4H2PO4/SiO2 was reused
in subsequent reactions without significant decrease
in activity even after five runs (Table 3).
Conclusions
We described herein an ammonium dihydrogen
phosphate adsorbed on silica gel (NH4H2PO4/SiO2)
catalyzed highly efficient, one-pot, green protocol for
the synthesis of a,á-bis(substituted-benzylidene) cy-
cloalkanones by the condensation of aromatic alde-
hydes and cyclic ketones under solvent-free condition
in very good to excellent yields. The present metho-
dology offers several advantages such as simple
procedure, low cost, easy work-up, short reaction
time, and milder condition.
Acknowledgements
We thank the faculty of chemistry of K.N. Toosi University
of Technology and Islamic Azad University-Marvdasht
Branch for supporting this work.
References
(1) Deli, J.; Lorand, T.; Szabo, D.; Foldesi, A. Pharmazie.
1984, 39, 539
540.
(2) Ogawa, M.; Ishii, Y.; Nakano, T.; Irifune, S. Jpn.
Kohai Tokkyo. 1988, JP 63192446 A2; Ogawa, M.;
Ishii, Y.; Nakano, T.; Irifune, S. Chem. Abstr. 1988,
63, 238034.

(3) Kawamata, J.; Inoue, K.; Inabe, T.; Kiguchi, M.;
Kato, M.; Taniguchi, Y. Chem. Phys. Lett. 1996, 249,
29
34.
(4) Dimmock, J.R.A.; Padmanilayam, M.P.; Zello, G.A.;
Nienaber, K.H.; Allen, T.M.; Santos, C.L.; De Clercq,
E.; Balzarini, J.; Manavathu, E.K.; Stables, J.P. Eur.
J. Med. Chem. 2003, 38, 169
177.
(5) Raj, A.A.; Raghunathan, R.; Sridevi Kumari, M.R.;
Raman, N. Bioorg. Med. Chem. 2003, 11, 407
419.
(6) Gangadhara, K.K. Polymer. 1995, 36, 1903
1910.
(7) Hathaway, B.A. J. Chem. Edu. 1987, 64, 367
368.
(8) Nakano, T.; Irifune, S.; Umano, S.; Inada, A.; Ishii,
Y.; Ogawa, M. J. Org. Chem. 1987, 52, 2239
2244.
(9) Irie, K.; Watanabe, K. Bull. Chem. Soc. Jpn. 1980, 53,
1366
1371.
(10) Nakano, T.; Migita, T. Chem. Lett. 1993, 22, 2157

2158.
(11) Iranpoor, N.; Kazemi, F. Tetrahedron. 1998, 54,
Downloaded by [Dalhousie University] at 03:39 02 January 2013
9475
9480.
(12) Bao, W.L.; Zhang, Y.M.; Taokai, Y. Synth.
Commun. 1996, 26, 503
507.
(13) Huang, D.F.; Wang, J.X.; Hu, Y.L. Chin. Chem.
Lett. 2003, 14, 333
334.
(14) Shinji, N.; Aki, M.; Fumiko, I.; Takayoshi, Y.;
Hiroshi, S.; Kiyoshi, S. J. Chem. Soc. Chem. Commun.
1990, 21, 1538
1539.
(15) Zhang, X.Y.; Fan, X.S.; Niu, H.Y.; Wang, J.J. Green
Chem. 2003, 5, 267
269.
(16) Salehi, P.; Khodaei, M.M.; Zolfigol, M.A.; Keyvan,
A. Monatsh. Chem. 2002, 133, 1291
1295.
(17) Cai, X.H.; Xie, B.; Guo, H. Chem. Pap. 2006, 60,
318
320.
(18) Wang, L.M.; Sheng, J.; Tian, H.; Han, J.; Fan, Z.;
Qian, C. Synthesis 2004, 3060
3064.
(19) Song, D.; Chen, Y.; Wang, R.; Liu, C.; Jiang, H.;
Luo, G. Prep. Biochem. & Biotech. 2009, 39, 201
207.
(20) Yang, L.; Lu, J.; Bai, Y.J. Chin. J. Org. Chem. 2003,
23, 659
661.
(21) Arnold, A.; Markert, M.; Mahrwald, R. Synthesis
2006, 1099
1102.
(22) An, L.T.; Zou, J.P.; Zhang, L.L. Catal. Commun.
2008, 9, 349
354.
Green Chemistry Letters and Reviews 259
(23) Ziarani, G.M.; Badiei, A.; Abbasi, A.; Farahani, Z.
Chin. J. Chem. 2009, 27, 1537
1542.
(24) Das, B.; Thirupathi, P.; Mahender, I.; Reddy, K.R.
J. Mol. Catal. A: Chem. 2006, 247, 182
185.
(25) Sabitha, G.; Reddy, G.S.K.; Reddy, K.B.; Yadav,
J.S. Synthesis 2004, 263
266.
(26) Bhagat, S.; Sharma, R.; Chakraborti, A.K. J. Mol.
Cata. A: Chem. 2006, 260, 235
240.
(27) Yadav, J.S.; Reddy, B.V.S.; Nagaraju, A.; Sarma,
J.A.R.P. Synth. Commun. 2002, 32, 893
896.
(28) Zhang, L.; Wang, S.; Sheng, E.; Zhou, S. Green
Chem. 2005, 7, 683
686.
(29) Hazarkhani, H.; Kumar, P.; Kondiram, K.S.; Shafi,
G.; Ikhlas, M. Synth. Commun. 2010, 40, 2887
2896.
(30) Zheng, M.; Wang, L.; Shao, J.; Zhong, Q. Synth.
Commun. 1997, 7, 351
354.
(31) Bigdeli, M.A.; Mahdavinia, G.H.; Jafari, S.;
Hazarkhani, H. Catal. Commun. 2007, 8, 2229
2231.
(32) Shrikhande, J.J.; Gawande, M.B.; Jayaram, R.V.
Catal. Commun. 2008, 9, 1010
1016.
(33) Singh, N.; Pandey, J.; Yadav, A.; Chaturvedi, V.;
Bhatnagar, S.; Gaikwad, A.N.; Sinha, S.K.; Kumar,
A.; Shukla, P.K.; Tripathi, R.P. Eur. J. Med. Chem.
2009, 44, 1705
1709.
(34) Solhy, A.; Amer, W.; Karkouri, M.; Tahir, R.;
Bouari, A.E.; Fihri, A.; Bousmina, M.; Zahouily, M.
J. Mol. Catal. A: Chem. 2011, 336, 8
15.
(35) Riadi, Y.; Mamouni, R.; Azzalou, R.; Boulahjar, R.;
Abrouki, Y.; El Haddad, M.; Routier, S.; Guillau-
met, G.; Lazar, S. Tetrahedron Lett. 2010, 51, 6715

6717.
(36) Wu, H.; Lin, W.; Wan, Y.; Xin, H.-Q.; Shi, D.-Q.;
Shi, Y.-H.; Yuan, R.; Bo, R.-C.; Yin, W. J. Comb.
Chem. 2010, 12, 31
34 and references cited therein.
(37) Lancaster, M. Green Chemistry: An Introductory
Text; Royal Society of Chemistry: Cambridge, 2002;
pp 87
96.
(38) M atlack, A.S. Introduction to Green Chemistry;
Marcel Dekker: New York-Basel, 2001; p 114, 191.
(39) Mahdavinia, G.H.; Rostamizadeh, Sh.; Amani, A.M.;
Emdadi, Z. Ultrason. Sonchem. 2008, 16, 7
10.
 260 G.H. Mahdavinia et al.

Appendix A: Supporting information for

O
Downloaded by [Dalhousie University] at 03:39 02 January 2013

O
Me

Me
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Cl OMe

O
O

Cl
OMe
Green Chemistry Letters and Reviews
261
Downloaded by [Dalhousie University] at 03:39 02 January 2013

262 G.H. Mahdavinia et al.

NO2

Me O
O

NO2
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Me
OMe

Me O
Me O

Me

OMe
Green Chemistry Letters and Reviews
263
Downloaded by [Dalhousie University] at 03:39 02 January 2013

264 G.H. Mahdavinia et al.

Cl

Me O
O

Cl
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Me

Me
Green Chemistry Letters and Reviews
265
Downloaded by [Dalhousie University] at 03:39 02 January 2013

266 G.H. Mahdavinia et al.

OMe

OMe
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Cl

Cl
Green Chemistry Letters and Reviews
267
Downloaded by [Dalhousie University] at 03:39 02 January 2013

268 G.H. Mahdavinia et al.

NO2

NO2
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Cl

Cl
Green Chemistry Letters and Reviews
269
Downloaded by [Dalhousie University] at 03:39 02 January 2013

270 G.H. Mahdavinia et al.

O
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Cl

Cl
Green Chemistry Letters and Reviews
271
Downloaded by [Dalhousie University] at 03:39 02 January 2013

272 G.H. Mahdavinia et al.

Me

Me
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Me O
Green Chemistry Letters and Reviews
273
Downloaded by [Dalhousie University] at 03:39 02 January 2013

274 G.H. Mahdavinia et al.

Me

Me O

Me
Downloaded by [Dalhousie University] at 03:39 02 January 2013

OMe

Me O

OMe
Green Chemistry Letters and Reviews
275
Downloaded by [Dalhousie University] at 03:39 02 January 2013

276 G.H. Mahdavinia et al.

Cl

Me O

Cl
Downloaded by [Dalhousie University] at 03:39 02 January 2013

Me O
Green Chemistry Letters and Reviews
277
Downloaded by [Dalhousie University] at 03:39 02 January 2013

278 G.H. Mahdavinia et al.

Me

Me O

Me
Downloaded by [Dalhousie University] at 03:39 02 January 2013

OMe

Me O

OMe
Green Chemistry Letters and Reviews
279
Downloaded by [Dalhousie University] at 03:39 02 January 2013

280 G.H. Mahdavinia et al.

Cl

Me O

Cl
 Downloaded by [Dalhousie University] at 03:39 02 January 2013

View publication stats

Green Chemistry Letters and Reviews
281