Preparative synthesis of functionally substituted esters of dehydroabietic and 4,4′-biphenyldicarboxylic acids

Article abstract of DOI:10.1007/s11176-005-0148-7

A preparative synthesis of functionally substituted esters of dehydroabietic and 4,4′-biphenylcarboxylic acids by the reaction of chlorides of these acids with alcohols in the presence of pyridine is developed. 4,4′-Biphenyldicarbonyl dichloride reacts with hydroperoxides to form peroxy esters and with lithium alcoholates, which allows preparation of the corresponding ethers derived from secondary and tertiary alcohols. 2004 MAIK "Nauka/Interperiodica".

Full text of DOI:10.1007/s11176-005-0148-7

Russian Journal of General Chemistry, Vol. 74, No. 8, 2004, pp. 1259 1263. Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 8, 2004,
pp. 1360 1364.
Original Russian Text Copyright
2004 by Dikusar, Yuvchenko, Kozlov, Ol’khovik, Potkin.
Preparative Synthesis of Functionally Substituted Esters
of Dehydroabietic and 4,4 -Biphenyldicarboxylic Acids
E. A. Dikusar, A. P. Yuvchenko, N. G. Kozlov, V. K. Ol’khovik, and V. I. Potkin
Institute of Chemistry of New Materials, National Academy of Sciences of Belarus, Minsk, Belarus
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus
Received October 2, 2002
Abstract A preparative synthesis of functionally substituted esters of dehydroabietic and 4,4 -biphenyl-
carboxylic acids by the reaction of chlorides of these acids with alcohols in the presence of pyridine is de-
veloped. 4,4 -Biphenyldicarbonyl dichloride reacts with hydroperoxides to form peroxy esters and with lithium
alcoholates, which allows preparation of the corresponding ethers derived from secondary and tertiary alcohols.
Esters of dehydroabietic and 4,4 -biphenyldicar-
boxylic acids (Ia and Ib), containing various func-
Me
tional groups, such as long-chain hydrocarbon frag-
Me
ments and acetylenic, aromatic, and bicyclic systems,
are interesting to study in terms of surfactant proper-
ties [1 3] and biological activity [4, 5]. In the present
work we describe the first convenient preparative
synthesis of functionally substituted dehydroabietic
and 4,4 -biphenyldicarboxylic esters IIIa IIIh and
IVa IVi, as well as peroxy esters IVj IVl obtained
by the reaction of dehydroabietic and 4,4 -biphenyldi-
carboxylic acid chlorides IIa and IIb with the cor-
responding alcohols, phenols, and hydroperoxides in
diethyl ether in the presence of pyridine [6]. The reac-
tion occurs in closed vessels in mild conditions at
room temperature within 24 36 h, requiring no pro-
longed stirring, heating and cooling and allowing the
starting materials to be mixed in any order.
Me
Me
ROH
Py
IIa
H
C OR
O
IIIa IIIh
III, R = Me(CH2)14 (a), Me(CH2)15 (b), HC CCH2 (c),
HC C(CH2)2 (d), HC C(CH2)3 (e),
Me
Me
Me
Me
Me
Me
H
Me
H
(h).
Me
Me
(f),
(g),
H
Me
H
Me
Me
Me
Me
Me
Me
SOCl2
C6H6
The preparative yield of esters IIIa IIIh and
peroxy esters IVa IVl is 77 91% (per purified target
product) (Table 1).
Me
H
C OH
H
C Cl
Dehydroabietyl chloride (IIa) is easily esterified
with primary and secondary alcohols, whereas 4,4 -bi-
phenyldicarbonyl dichloride (IIb) reacts in mild
conditions only with primary alcohols, phenols, and
hydroperoxides [5, 7, 8]. To react dichloride IIb with
secondary and tertiary alcohols Va Vd, the latter were
first converted to lithium alcoholates VIa VId by
treatment with butyllithium in benzene. Lithium al-
coholates VIa VId are fairly reactive compounds [9]
O
O
Ia
HOOC
IIa
COOH
Ib
SOCl2
C6H6
ClOC
COCl
IIb
1070-3632/04/7408-1259 2004 MAIK Nauka/Interperiodica

1260
DIKUSAR et al.
Table 1. Properties of esters IIIa IIIh, IVa IVi, and VIIa VIId and peroxy esters IVj IVl
Found, %
Calculated
M
Comp.
no.
Yield,
%
mp,
C
Formula
C
H
C
H
found
calculated
IIIaa
IIIbb
IIIcc
IIIdd
IIIee
IIIff
IIIg
IIIh
IVa
IVb
IVc
IVd
IVe
IVf
IVg
IVh
IVi
80
83
79
81
82
78
79
77
81
84
86
83
91
90
80
81
82
81
80
84
81
79
81
79
82.58
82.61
81.92
82.04
82.28
82.44
82.60
82.63
78.44
80.19
80.43
80.40
75.51
76.48
77.18
70.71
71.50
68.45
71.22
69.30
78.91
79.58
77.23
79.65
11.67
11.70
9.44
9.46
9.71
10.71
10.32
10.28
9.78
10.91
11.03
11.20
4.61
5.44
6.19
4.52
5.01
6.91
5.70
6.72
9.16
8.41
6.18
8.30
C35H58O2
C36H60O2
C23H30O2
C24H32O2
C25H34O2
C30H46O2
C30H44O2
C30H44O2
C34H50O4
C44H70O4
C46H74O4
C48H78O4
C20H14O4
C22H18O4
C24H22O4
C30H22O8
C32H26O8
C22H26O6
C24H22O6
C30H34O8
C34H46O4
C34H42O4
C24H22O4
C34H42O4
82.29
82.38
81.61
81.77
81.92
82.14
82.52
82.52
78.12
79.71
79.95
80.17
75.46
76.29
76.99
70.58
71.37
68.38
70.93
68.95
78.72
79.34
76.99
79.34
11.44
11.52
9.16
9.15
9.55
10.57
10.16
10.16
9.64
10.64
10.79
10.93
4.43
5.24
5.92
4.34
4.87
6.78
5.46
6.56
8.94
8.22
5.92
8.22
498.6
508.4
320.0
338.1
352.3
420.7
421.8
420.0
508.2
644.1
673.2
698.0
306.9
310.2
360.4
492.3
519.1
367.9
388.7
491.1
504.6
489.5
360.0
496.2
510.8
524.9
338.5
352.5
366.5
438.7
436.7
436.7
522.8
663.0
691.1
719.1
318.3
346.4
374.4
510.5
538.6
386.4
406.4
522.6
518.7
514.7
374.4
514.7
145 146
152 153
63 64
84 85
89 90
64 65
135 136
116 117
79 80
176 177
144 145
121 122
95 96
IVj
IVk
IVl
27 28
VIIag
VIIb
VIIc
VIId
196 197
114 115
171 172
a
f
20
20
b
20
20
d
20
c
20
20
d
20
20
e
20
20
d
d
0.9376, n 1.5110.
d
g
0.9459, n 1.5080.
d
0.9710, n 1.5500.
d
0.9648, n 1.5365.
d
0.9620, n 1.5375.
20
20
20
D
D
20
D
20
D
20
D
20
20
20
0.9744, n 1.5250.
1.0316, n 1.5370.
D
20
D
Me
ROH
COOR
ROOC
Me
Me
(b),
IIb
Me
Py
H
IVa IVl
(a),
V VII, R =
H
IV, R = Me(CH2)9 (a), Me(CH2)14 (b), Me(CH2)15 (c),
Me(CH2)16 (d), HC CCH2 (e), HC C(CH2)2 (f),
H
Me
Me
EtO
MeO
Me
‹
›
‹
›
‹
›
HC C(CH2)3 (g),
CHO (i),
CHO (h),
‹
›
›
‹
HC CCMe2 (c), Me
(d).
›
‹
Me
Me3CO (j), HC CMe2CO (k), HOMe2CC CCMe2O (l).
and readily react with dichloride IIb to form esters
VIIa VIId in 79 81% yields.
BuLi
R Me2COH
R Me2COLi
C4H10
The esters and peroxy esters are viscous liquids
(IIIa IIIf, VIIa) or crystals (IIIg, IIIh, IVa IVl,
VIIb VIId). The properties of the synthesized com-
Va Vd
VIa VId
2VIa VId
1
pounds are presented in Table 1, and the H and IR
IIb
COOR
R OOC
spectra confirmative of their structures [10, 11], in
Tables 2 and 3.
VIIa VIId
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 8 2004

PREPARATIVE SYNTHESIS OF FUNCTIONALLY SUBSTITUTED ESTERS
1261
1
Table 2. H NMR spectra of chlorides IIa and IIb, esters IIIa IIIh, IVa IVi, and VIIa VIId, and peroxy esters IVj IVl
Comp.
no.
1H NMR spestrum, , ppm
IIa
1.21 d (6H, Me2C), 1.21 s (3H, Me), 1.36 s (3H, Me), 1.40 3.15 m [12H, 2CH, (CH2)2 and (CH2)3], 6.75 7.30 m
(3H, C6H3)
IIb
7.50 8.20 m (8H, 2C6H4)
IIIa
0.87 t [3H, Me(CH2)14], 1.15 d (6H, Me2C), 1.00 3.00 m [44H, 2Me, 2CH, (CH2)2, (CH2)3 and (CH2)13], 4.00 t
(2H, CH2O), 6.80 7.15 m (3H, C6H3)
IIIb
IIIc
IIId
IIIe
IIIf
0.87 t [3H, Me(CH2)15], 1.15 d (6H, Me2C), 1.00 2.95 m [46H, 2Me, 2CH, (CH2)2, (CH2)3, and (CH2)14], 4.02 t
(2H, CH2O), 6.75 7.15 m (3H, C6H3)
1.12 1.30 m (12H, 4Me), 1.10 3.00 m [12H, 2CH, (CH2)2 and (CH2)3], 2.42 t (1H, C CH), 4.64 t (2CH, CH2O),
6.80 7.20 m (3H, C6H3)
1.10 1.25 m (12H, 4Me), 1.10 2.95 m [15H, C CH, 2CH, CH2, (CH2)2, and (CH2)3], 4,12 t.d (2H, CH2O), 6.75
7.20 m (3H, C6H3)
1.10 1.30 m (12H, 4Me), 1.10 3.00 [17H, C CH, 2CH, 2(CH2)2, and (CH2)3], 4.15 t (2CH, CH2O), 6.75 7.20 m
(3H, C6H3)
0.65 0.90 m (9H, 3Me), 1.15 1.25 m (12H, 4Me), 1.10 2.95 m [21H, 5CH, CH2, 2(CH2)2, and (CH2)3], 4.65 d.t
(1H, CHO), 6.80 7.15 m (3H, C6H3)
IIIg
IIIh
0.75 0.90 m (9H, 3Me), 1.15 1.30 m (12H, 4Me), 1.10 2.95 m [19H, 3CH, CH2, 2(CH2)2, and (CH2)3],
4.85 d.d.d (1H, CHO), 6.80 7.20 m (3H, C6H3)
0.75 0.95 m (9H, 3Me), 1.10 1.25 m (12H, 4Me), 1.10 2.95 m [19H, 3CH, CH2, 2(CH2)2, and (CH2)3],
4.65 d.d.d (1H, CHO), 6.80 7.20 m (3H, C6H3)
IVa
IVb
IVc
IVd
IVe
IVf
IVg
IVh
IVi
0.86 t (6H, 2Me), 1.15 1.90 m [32H, 2(CH2)8], 4.33 t (4H, 2CH2O), 7.55 8.25 m (8H, 2C6H4)
0.89 t (6H, 2Me), 1.15 1.95 m [52H, 2(CH2)13], 4.36 t (4H, 2CH2O), 7.60 8.20 m (8H, 2C6H4)
0.89 t (6H, 2Me), 1.10 1.95 m [56H, 2(CH2)14], 4.35 t (4H, 2CH2O), 7.60 8.20 m (8H, 2C6H4)
0.89 t (6H, 2Me), 1.10 1.95 m [60H, 2(CH2)15], 4.37 t (4H, 2CH2O), 7.55 8.25 m (8H, 2C6H4)
2.52 t (2H, 2C CH), 4.94 d (4H, 2CH2O), 7.55 8.20 m (8H, 2C6H4)
2.02 t (2H, 2C CH), 2.68 t.d (4H, CH2C C), 4.45 t (4H, 2CH2O), 7.55 8.20 m (8H, 2C6H4)
1.85 2.50 m [10H, 2C CH and (CH2)2], 4.45 t (4H, 2CH2O), 7.60 8.20 m (8H, 2C6H4)
(6H, 2MeO), 7.30 8.40 m (14H, 2C6H3 and 2C6H4), 9.98 s (2H, 2CHO)
1.33 t (6H, 2Me), 4.14 q (4H, 2CH2O), 7.25 8.35 m (14H, 2C6H3 and 2C6H4), 9.95 s (2H, 2CHO)
1.44 s (18H, 2Me3COO), 7.55 8.15 m (8H, 2C6H4)
IVj
IVk
IVl
VIIa
1.69 s (12H, 2Me2COO), 2.55 s (2H, 2C CH), 7.55 8.15 m (8H, 2C6H4)
1.43 s (12H, 2Me2C), 1.65 s (12H, 2Me2COO), 4.35 br.s (2H, 2OH), 7.50 8.20 m (8H, 2C6H4)
0.60 0.95 m (18H, 6Me), 0.80 2.25 m [18H, 6CH, 2CH2, 2(CH2)2], 4.95 d.t (2H, 2CHO), 7.50 8.20 m (8H,
2C6H4)
VIIb
VIIc
VIId
0.85 1.15 m (18H, 6Me), 1.10 2.00 m [14H, 2CH, 2CH2, 2(CH2)2], 4.92 t (2H, 2CHO), 7.55 8.15 m (8H, 2C6H4)
1.83 s (12H, 2Me2C), 2.59 s (2H, 2C CH), 7.55 8.20 m (8H, C6H4)
0.80 2.40 m [14H, 2CH, 2CH2 and 2(CH2)2], 1.59 d (12H, 2Me2C), 2.06 d (6H, 2Me), 5.40 br.s (2H, 2=CH),
7.50 8.15 (8H, 2C6H4)
EXPERIMENTAL
The IR spectra were recorded on a Nicolet Protege-
Dehydroabietic and 4,4 -biphenyldicarboxylic
acid chlorides IIa and IIb were synthesized by
refluxing acids Ia and Ib with a 1.5-fold (Ia) or 3-fold
460 Fourier spectrometer for thin films (IIIa IIIf, IVl, (Ib) excess of SOCl2 in benzene [12]. Hydroperoxides
and VIIa) or KBr pellets (IIIg, IIIh, IVa IVk, and
VIIb VIIe). The H NMR spectra were obtained on a
were prepared by the procedures in [13 15] and
butyllithium, by the procedure in [16].
1
Tesla BS-567A spectrometer (100 MHz) for 5% solu-
tions in CDCl3. The molecular weights were deter-
mined by cryoscopy in benzene. Column chromato-
graphy was performed on neutral Al2O3 (Brockmann
activity grade II).
Esters and peroxy esters of dehydroabietic and
4,4 biphenyldicarboxylic acids IIIa IIIh and IVa
IVl (general procedure). Anhydrous pyridine,
3.5 mmol, was added to a solution of 3 mmol de-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 8 2004

1262
DIKUSAR et al.
Table 3. IR spectra of esters IIIa IIIh, IVa IVi, and VIIa VIId and peroxy esters IVj IVl
Comp.
no.
1
IR spectrum, , cm
IIIa 3075, 3050 (CHAr); 2954, 2925, 2854 (CHAlk); 1725 (C=O); 1610, 1500 (Ar); 1466 (CH2); 1244, 1125 (C O);
820, 720 (CHAr)
IIIb 3075, 3050 (CHAr); 2950, 2925, 2853 (CHAlk); 1725 (C=O); 1610, 1500 (Ar); 1470 (CH2); 1245, 1130 (C O);
820, 720 (CHAr)
IIIc 3277 ( C H); 3070, 3050 (CHAr); 2955, 2932, 2869 (CHAlk); 2130 (C C); 1732 (C=O); 1610, 1498 (Ar); 1460
(CH2); 1239, 1122 (C O); 822, 725 (CHAr)
IIId 3290 ( C H); 3075, 3050 (CHAr), 2957, 2930, 2869 (CHAlk); 2125 (C C); 1725 (C=O); 1610, 1498 (Ar); 1459
(CH2); 1243, 1124 (C O); 823, 725 (CHAr)
IIIe 3290 ( C H); 3075, 3050 (CHAr); 2956, 2931, 2869 (CHAlk); 2120 (C C); 1724 (C=O); 1610, 1498 (Ar); 1460
(CH2); 1245, 1125 (C O); 823, 725 (CHAr)
IIIf 3075, 3050 (CHAr); 2955, 2930, 2865 (CHAlk); 1720 (C=O); 1610, 1500 (Ar); 1460 (CH2); 1246, 1125 (C O);
820, 725 (CHAr)
IIIg 3075, 3045 (CHAr); 2980, 2952, 2930, 2868 (CHAlk); 1717 (C=O); 1610, 1500 (Ar); 1470, 1453 (CH2); 1245,
1109 (C O); 825 (CHAr)
IIIh 3075, 3045 (CHAr); 2954, 2932, 2871 (CHAlk); 1716 (C=O); 1610, 1500 (Ar); 1468, 1455 (CH2); 1244, 1109
(C O); 825 (CHAr)
IVa 3095, 3060 (CHAr); 2953, 2917,2870, 2850 (CHAlk); 1717 (C=O); 1610, 1560 (Ar); 1475, 1470 (CH2); 1290,
1121 (C O); 840, 750, 720, 695 (CHAr)
IVb 3090, 3065 (CHAr); 2955, 2920, 2870, 2850 (CHAlk); 1710 (C=O); 1610, 1560 (Ar); 1470 (CH2); 1280, 1125
(C O); 845,755 (CHAr)
IVc 3090, 3065 (CHAr); 2955, 2915, 2870, 2850 (CHAlk); 1720 (C=O); 1610, 1560 (Ar); 1480, 1470 (CH2); 1290,
1125 (C O); 845, 750 (CHAr)
IVd 3090, 3070 (CHAr); 2955, 2918, 2849 (CHAlk); 1720 (C=O); 1610, 1560 (Ar); 1472, 1460 (CH2); 1285, 1116
(C O); 845, 755 (CHAr)
IVe 3274 ( C H); 3090, 3070 (CHAr); 2980, 2950, 2925, 2875, 2860 (CHAlk); 2130 (C C); 1711 (C=O); 1607, 1560
(Ar); 1445 (CH2); 1283, 1120 (C O); 843, 753 (CHAr)
IVf
3260 ( C H); 3085, 3070, 3050 (CHAr); 2980, 2970, 2920, 2850 (CHAlk); 2120 (C C); 1715 (C=O); 1607, 1560
(Ar); 1470, 1435 (CH2); 1264, 1116 (C O); 845, 753 (CHAr)
IVg 3256 ( C H); 3090, 3070, 3045 (CHAr); 2980, 2960, 2930, 2890, 2855 (CHAlk); 2115 (C C); 1711 (C=O); 1608,
1560 (Ar); 1460, 1440 (CH2); 1281, 1121 (C O); 845, 756 (CHAr)
IVh 3095, 3069, 3050, 3030, 3014 (CHAr); 2985, 2953, 2922, 2852, 2825, 2775, 2725 (CHAlk); 1740 (C=O); 1697
(HC=O); 1602, 1560, 1505, 1470 (Ar); 1285, 1260, 1151, 1107, 1066, 1027 (C O); 872, 845, 811, 779, 750, 676
(CHAr)
IVi
3090, 3073, 3055, 3035 (CHAr); 2986, 2942, 2890, 2875, 2836, 2785, 2730 (CHAr); 1732 (C=O); 1699 (HC=O);
1603, 1588, 1560, 1508, 1478 (Ar); 1435(CH2); 1289, 1260, 1197, 1157, 1111, 1070, 1039, 1005 (C O); 870,
844, 806, 784, 748, 697, 679 (CHAr)
IVj
3080, 3060 (CHAr); 2978, 2940, 2870(CHAlk);1753 (C=O); 1607, 1560(Ar);1239, 1059(C O);845, 749, 695(CHAr)
IVk 3234 ( C H); 3090, 3070 (CHAr); 3003, 2985, 2955, 2924, 2860 (CHAlk); 2108 (C C); 1748 (C=O); 1604, 1560
(Ar); 1234, 1064 (C O); 845, 748, 690 (CHAr)
IVl
3373 (OH); 3090, 3070, 3040 (CHAr); 2984, 2936, 2870 (CHAlk); 1759 (C=O); 1606, 1560 (Ar); 1235, 1170,
1147, 1054, 1018, 1005, 952 (C O); 838, 749, 693, 682 (CHAr)
VIIa 3075, 3045 (CHAr); 2955, 2927, 2869 (CHAlk); 1716 (C=O); 1608, 1560 (Ar); 1456 (CH2); 1285, 1112 (C O);
847, 759, 700 (CHAr)
VIIb 3080, 3065, 3040 (CHAr); 3002, 2980, 2954, 2878 (CHAlk); 1709 (C=O); 1607, 1580 (Ar); 1470, 1455 (CH2);
1280, 1109 (C O); 840, 758, 655, 645 (CHAr)
VIIc 3286 ( C H); 3070, 3045, 3030 (CHAr); 2980, 2945, 2930, 2860 (CHAlk); 2120 (C C); 1720 (C=O); 1605, 1560
(Ar); 1283, 1102 (C O); 851, 761, 684, 652, 636 (CHAr)
VIId 3070, 3050, 3035 (CHAr); 3010 (=¢ H), 2980, 2965, 2945, 2925, 2945, 2860, 2840 (CHAlk); 1702 (C=O); 1605,
1565 (Ar); 1470, 1460, 1440 (CH2); 1287, 1119 (C O); 850, 800, 761, 705 (CHAr)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 8 2004

PREPARATIVE SYNTHESIS OF FUNCTIONALLY SUBSTITUTED ESTERS
1263
hydroabietyl chloride (with compound IIa) or
1.5 mmol of 4,4 -biphenyldicarbonyl dichloride (with
compound IIb) and 3 mmol of corresponding alcohols,
phenols, or hydroperoxides in 100 ml of absolute di-
ethyl ether. The reaction mixture was slightly shaken
and left to stand at 18 23 C for 24 36 h. The pre-
cipitate of pyridine hydrochloride was filtered off and
washed with 50 mlof ether. The filtrate was washed
with water and saturated aqueous sodium hydrocar-
bonate, and dried with CaCl2. The ether was removed
by distillation, and the residue was subjected to a
vacuum. Esters IIIa IIIf were purified by column
chromatography on Al2O3, eluent hexane; compounds
IIIg, IIIh, and IVa IVl were purified by low-tem-
perature crystallization from benzene hexane.
3. Fizika tonkikh plenok. Sovremennoe sostoyanie issle-
dovanii i tekhnologicheskie primeneniya (Physics of
Thin Films. Modern State of Research and Techno-
logical Applications), Moscow: Mir, 1977, vol. 7,
p. 340.
4. Schulte, K. and Rucker, G., Prog. Drug. Res., 1970,
vol. 14, p. 387.
5. Comprehensive Organic Chemistry, Barton, D.H. and
Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2.
Translated under the title Obshchaya organicheskaya
khimiya, Moscow: Khimiya, 1982, vol. 4.
6. Dikusar, E.A., Yuvchenko, A.P., Zvereva, T.D.,
Makhnach, S.A., and Filanchuk, L.P., Zh. Obshch.
Khim., 1996, vol. 66, no. 11, p. 1813.
Esters VIIa VIId (general procedure). A solution
of 3 mmol of butyllithium in benzene was added with
vigorous stirring under argon over the course of 0.5 h
to a solution of 3 mmol of secondary or tertiary al-
cohol Va Ve. The solution of lithium alcoholate
VIa VIe was stirred for 2 h, after which 1.5 mmol of
dichloride IIb was added to it in one portion. The
mixture was stirred for 8 12 h and left to stand at
18 23 C for 24 36 h. The precipitate of lithium chlo-
ride was filtered off and washed with 50 ml of ben-
zene. The filtrate was washed with water and saturated
aqueous sodium hydrocarbonate. The solvent was
removed by distillation, and the residue was subjected
to a vacuum. Ester VIIa was purified by column
chromatography on Al2O3, eluent hexane; compounds
VIIb VIIe were purified by low-temperature crystal-
lization from benzene hexane.
7. Ingold, C.K., Structure and Mechanism in Organic
Chemistry, Ithaca: Cornell Univ., 1969, 2nd ed.
8. Houben-Weyl, Methoden der organischen Chemie,
1985, vol. E5, part 1.
9. Yuvchenko, A.P., Dikusar, E.A., and Moisei-
chuk, K.L., Zh. Obshch.Khim., 1994, vol. 64, no. 1,
p. 81.
10. Bellami, L. and Bellamy, L.J., The Infra-red Spectra
of Complex Molecules, London: Methuen, 1958.
11. Gordon, A. and Ford, R., The Chemist s Companion,
New York: Wiley, 1972.
12. Monomery dlya polikondensatsii (Monomers for Poly-
condensation), Korshak, V.V., Ed., Moscow: Mir,
1976.
13. Antonovskii, V.L., Organicheskie perekisnye initsi
atory (Organic Peroxide Initiators), Moscow: Khimiya,
1972.
ACKNOWLEDGMENTS
The work was financially supported by the Bela-
russian Republican Foundation for Basic Research
(grant no. X 03-079) and INTAS (grant no. 99-
00806).
14. Milas, N.A. and Mageli, O.L., J. Am. Chem. Soc.,
1952, vol. 74, no. 7, p. 1471.
15. Yuvchenko, A.P., Moiseichuk, K.L., Dikusar, E.A.,
and Ol’dekop, Yu.A., Vesci Akad. Navuk BSSR, Ser.
Khim. Navuk, 1983, vol. 3, p. 60.
REFERENCES
16. Talalaeva, T.V. and Kocheshkov, K.A., Metody ele-
mentoorganicheskoi khimii. Litii, natrii, kalii, rubidii,
tsezii (Methods of Organoelement Chemistry. Lithium,
Sodium, Potassium, Rubidium, Cesium), Moscow:
Nauka, 1971, book. 1, pp. 99, 554.
1. Gaines, G.L., Insoluble Monolayers at Liquid Gas
Interfaces, New York: Wiley Interscience, 1966.
2. Jaycock, M.J. and Parfitt, G.D., Chemistry of Inter-
fases, New York: Wiley, 1981.
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