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M. Tajbakhsh et al.
LETTER
R1
R1
R2
2–
N+ +N
SO4
2–
S2O8
H2O, reflux
N+ +N
n
OH +
+
O +
n
R2
insoluble in water
soluble in water
2–
SO4
2
H O, r.t.
2–
N+ +N
soluble in water
(K S O )
2
2
8 aq
N+ +N
S O
8
+
(K2SO4)aq
+
2
n
n
insoluble in water
Scheme 3
Acknowledgment
(4) Hinzen, A.; Lenz, K.; Ley, S. V. Synthesis 1999, 977.
(
(
5) Tamami, B.; Godarzian, N. Eur. Polym. J. 1992, 28, 1035.
6) Godarzian, N.; Ghahramani, P.; Hosini, S. Polym. Int. 1996,
Financial support of this work from the Research Council of
Mazandaran University is gratefully acknowledged.
3
9, 61.
7) Suresh, S.; Skaria, S.; Pontrathnam, S. Synth. Commun.
996, 26, 2113.
8) Minghu, W.; Guichun, Y.; Zuxing, C. React. Funct. Polym.
000, 44, 97.
9) Preparation of {-N (CH ) CH CH N [(CH ) ](CH ) -}
(
(
(
1
References and Notes
2
(
1) Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis,
Vol. 1–11; Wiley: New York, 1967-1984.
+
+
3 2
2
2
3 2
2 4
n
2
–
S2O (P-S O ).
(
2) (a) Anastas, P. T.; Williamson, T. C. Green Chemistry:
Frontiers in Benign Chemical Synthesis and Processes;
Oxford University Press: Oxford, 1998. (b) Curzons, A. D.;
Constable, D. C. J.; Mortimer, D. N.; Cunningham, V. L.
Green Chem. 2001, 3, 1.
8
2
8
To an aqueous solution of polymer (1 g, 5 mL of H O) was
2
added a solution of K S O (1.62 g, 6 mmol in 30 mL of
2
2
8
H O). The mixture was stirred at r.t. for 30 min. The
2
resulting white solid was filtered, washed with distilled H O
2
(
10 mL) and dried over CaCl in a desiccator under vacuum.
(
3) (a) Corey, E. J.; Boger, D. L. Tetrahedron Lett. 1978, 19,
2
2
–
The content of active oxidizing agent (S O ) was
2461. (b) Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979,
20, 399. (c) Guziec, F. S.; Luzzio, F. A. Synthesis 1980,
691. (d) Bhattacharjee, M. N.; Chaudhuri, M. K.; Dasgupta,
2
8
8
determined by titration.
10) Typical Procedure for Oxidation of Alcohols and
Hydroquinone with P-S O .
(
H. S.; Roy, N. Synthesis 1982, 588. (e) Santeniello, E.;
Milani, F.; Casati, R. Synthesis 1983, 749. (f) Rajkumar, G.
A.; Murugesan, V. Synth. Commun. 1999, 29, 2105.
2
8
A mixture of alcohol or hydroquinone (1 mmol), H O (10
2
mL) and P-S O (0.36 g, ca. 1 mmol) was placed in a 25-mL
2
8
round-bottom flask and was stirred and heated to reflux.
After completion of the reaction (monitored by TLC), the
(
g) Tajbakhsh, M.; Ghaemi, M.; Sarabi, M.; Ghassemzadeh,
M.; Heravi, M. M. Monatsh. Chem. 2000, 131, 1213.
h) Mahjoub, A. R.; Ghammami, Sh.; Kassaee, M. Z.
reaction mixture was cooled, and extracted with Et O
(
2
(
3 × 10 mL). The combined organic layers were washed with
Tetrahedron Lett. 1975, 16, 2647. (i) Tajbakhsh, M.;
Hosseinzadeh, R.; Yazdani-Niaki, M. J. Chem. Res., Synop.
brine, dried over anhyd Na SO , and solvent evaporated
2
4
under reduced pressure. The crude product was purified by
column chromatography on silica gel to afford pure material.
2
002, 10, 508. (j) Tajbakhsh, M.; Hosseinzadeh, R.;
Yazdani-Niaki, M. Tetrahedron Lett. 2002, 43, 9413.
k) Tajbakhsh, M.; Hosseinzadeh, R.; Sadatshahabi, M.
(
11) Typical Procedure for Recycled P-S O .
(
2 8
The solvated polymer in aqueous phase after completion of
the reaction was washed with Et O and recycled with added
Synth. Commun. 2005, 35, 1547. (l) Tajbakhsh, M.;
Lakouraj, M. M.; Yadoolahzadeh, K. Phosphorus, Sulfur
Silicon Relat. Elem. 2005, 180, 2431. (m) Shirini, F.;
Mohammadpoor-Baltork, I.; Hejazi, Z.; Heravi, P. Bull.
Korean Chem. Soc. 2003, 24, 517. (n) Alessandro, N.;
Liberatore, L.; Tonucci, L.; Morvillo, A.; Bressan, M. J.
Mol. Catal. A: Chem. 2001, 175, 83. (o) Firozabadi, H.;
Salehi, D.; Mohamadpour-Baltork, I. Bull. Chem. Soc. Jpn.
2
solution of K S O (in H O). The resulting white solid
2
2
8
2
product was filtered, washed with Et O (3 × 10 mL) and
2
cooled distilled H O (10 mL) and dried over CaCl in a
2
2
desiccator under vacuum for subsequent reaction.
(
(
12) John, W.; Son, I. Polym. Lett. Ed. 1977, 15, 31.
13) House, D. A. Chem. Rev. 1962, 185.
1991, 65, 2879. (p) Jung, J. C.; Choi, H. C.; Kim, Y. H.
Tetrahedron Lett. 1993, 7, 3581. (q) Hajipour, A. R.;
Mohammadpour-Baltork, I.; Kianfar, G. Bull. Chem. Soc.
Jpn. 1998, 71, 2655. (r) Mohammadpoor, I.; Hajipour, A.
R.; Mohammadi, H. Bull. Chem. Soc. Jpn. 1998, 71, 1649.
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