Long-chain functionally substituted aromatic Schiff bases derived from cetylamine

Article abstract of DOI:10.1134/S1070428009100108

New long-chain functionally substituted aromatic Schiff bases containing alkoxy and acyloxy groups, as well as carborane fragments, were synthesized by condensation of the corresponding benzaldehydes of the vanillin series with cetylamine.

Full text of DOI:10.1134/S1070428009100108

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 10, pp. 1481–1487. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © E.A. Dikusar, V.I. Potkin, N.G. Kozlov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 10, pp. 1496–1502.
Long-Chain Functionally Substituted Aromatic Schiff Bases
Derived from Cetylamine
E. A. Dikusar, V. I. Potkin, and N. G. Kozlov
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
ul. Surganova 13, Minsk, 220072 Belarus
e-mail: potkin@ifoch.bas-net.by
Received December 25, 2008
Abstract—New long-chain functionally substituted aromatic Schiff bases containing alkoxy and acyloxy
groups, as well as carborane fragments, were synthesized by condensation of the corresponding benzaldehydes
of the vanillin series with cetylamine.
DOI: 10.1134/S1070428009100108
We previously reported on the synthesis of reactions were carried out in boiling anhydrous methyl
(E)-N-(4-acyloxy-3-alkoxybenzylidene)octadecan-1-
amines [1]. Long-chain aromatic Schiff bases are
alcohol, and long-chain aromatic Schiff bases IIIa–
IIIv and IVa–IVm were isolated in 87–94% yield
promising compounds for the preparation of vacuum- (Scheme 1). The products were sufficiently pure (they
deposited nanofilms and Langmuir–Blodgett films contained no impurities of initial compounds), and no
necessary for the manufacture of nanomaterials based additional purification was necessary.
thereon [2, 3].
Compounds III and IV are colorless or slightly
The goal of the present work was to develop a pro- colored low-melting crystalline substances. Their
cedure for the preparation of new long-chain func- structure was confirmed by the data of elemental
tionally substituted aromatic Schiff bases containing analysis, cryoscopic determination of the molecular
1
alkoxy and acyloxy groups and carborane fragments. weight, and IR, UV, and H NMR spectra. The azo-
1
methine proton (HC=N) resonated in the H NMR
spectra of III and IV as a singlet at δ 8.16–8.25 ppm,
which is typical of E configuration about the C=N
Compounds IIIa–IIIv and IVa–IVm were synthesized
by condensation of the corresponding substituted benz-
aldehydes I of the vanillin series with cetylamine (II)
which is used as flotation agent in industry [4]. The bond [5].
Scheme 1.
R
CHO
R
C16H33
N
MeOH, Δ
+
C
16H33NH2
R'O
R'O
I
II
IIIa–IIIu, IVa–IVl
C16H33
R
O
N
O
O
N
O
R
C16H33
IIIv, IVm
III, R = H, R′ = Me (a); R = MeO, R′ = H (b), Me (c), MeC(O) (d), EtC(O) (e), PrC(O) (f), Me2CHC(O) (g), Me(CH2)6C(O) (h),
Me(CH2)8C(O) (i), Me(CH2)16C(O) (j), H2C=C(Me)C(O) (k), PhCH2C(O) (l), PhCH(Me)CH2C(O) (m), PhC(O) (n), 2,4-Cl2-
C6H3C(O) (o), 4-BrC6H4C(O) (p), 3-O2NC6H4C(O) (q), MeOC(O) (r), EtOC(O) (s), o-C2B10H11C(O) (t), m-C2B10H11C(O) (u); R =
MeO (v); IV, R = EtO, R′ = H (a), Me (b), MeC(O) (c), EtC(O) (d), PrC(O) (e), Me2CHC(O) (f), Me2CHCH2C(O) (g),
4-Me-C6H4C(O) (h), MeOC(O) (i), EtOC(O) (j), o-C2B10H11C(O) (k), m-C2B10H11C(O) (l); R = EtO (m).
1481

DIKUSAR et al.
3425 (OH); 3070, 3060, 2998 (C–Harom); 2954, 2919,
1482
EXPERIMENTAL
2850 (C–Haliph); 1646 (C=N); 1590, 1516, 1430
(C=Carom); 1468 (CH2); 1285, 1230, 1029, 1029
(C–O); 870, 824, 780, 740, 721 (δC–Harom). UV spec-
trum, λmax, nm (ε): 208 (12000), 225 (9000), 267
The IR spectra were recorded in KBr on a Nicolet
Protégé-460 spectrometer with Fourier transform. The
UV spectra were measured on a Specord UV-Vis spec-
trophotometer from 1×10–4 M solutions in methanol.
1
(10000), 303 (7000). H NMR spectrum, δ, ppm:
1
The H NMR spectra were obtained on a Tesla BS-
0.92 t (3H, Me), 1.10–2.00 m (28H, CH2), 3.64 t (2H,
CH2N), 3.94 s (3H, MeO), 6.60 br.s (1H, OH), 6.98–
7.50 m (3H, Harom), 8.16 s (1H, CH=N). Found, %:
C 77.04; H 11.14; N 3.48. M 362.8. C24H41NO2. Cal-
culated, %: C 76.75; H 11.00; N 3.73. M 375.6.
587A instrument operating at 100 MHz from 5% so-
lutions in chloroform-d using tetramethylsilane as in-
ternal reference. The elemental compositions were de-
termined with an accuracy of ±0.1% on an Elementar
Vario EL-III C,H,N,O,S analyzer. The molecular
weights were determined by cryoscopy in benzene.
(E)-N-(3,4-Dimethoxybenzylidene)hexadecan-1-
amine (IIIc). Yield 90%, mp 48–49°C. IR spectrum, ν,
cm–1: 3080, 3004 (C–Harom); 2955, 2916, 2850
(C–Haliph); 1641 (C=N); 1602, 1585, 1514, 1419
(C=Carom); 1471 (CH2); 1265, 1239, 1163, 1137, 1022
(CO); 872, 811, 740, 715 (δC–Harom). UV spectrum,
Initial alkoxy- and acyloxy-substituted benzalde-
hydes I were synthesized according to the procedures
described in [6–11]; commercial cetylamine (II) of
analytical grade had a purity of 99%, mp 45–46°C.
λ
max, nm (ε): 207 (12000), 226 (11000), 268 (11000),
Schiff bases IIIa–IIIu and IVa–IVl (general
procedure). A solution of 5 mmol of the corresponding
aldehyde I and 5 mmol of cetylamine (II) in 30 ml of
anhydrous methanol was heated for 20 min under
reflux. The hot solution was filtered through a folded
filter paper, the filtrate was cooled and left to stand for
10–15 h at 5°C, and the precipitate was filtered off
through a glass filter, washed with a small amount of
methanol, and dried in air.
1
305 (7000). H NMR spectrum, δ, ppm: 0.91 t (3H,
Me), 1.10–2.05 m (28H, CH2), 3.64 t (2H, CH2N),
3.92 s (3H, 3-MeO), 3.95 s (3H, 4-MeO), 6.90–7.45 m
(3H, Harom), 8.17 s (1H, CH=N). Found, %: C 77.29;
H 11.15; N 3.26. M 381.3. C25H43NO2. Calculated, %:
C 77.07; H 11.12; N 3.59. M 389.6.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
acetate (IIId). Yield 94%, mp 47–48°C. IR spectrum,
ν, cm–1: 3068, 3013 (C–Harom); 2953, 2915, 2849
(C–Haliph); 1765 (C=O); 1644 (C=N); 1601, 1598,
1514, 1374 (C=Carom); 1472 (CH2); 1289, 1268, 1222,
1164, 1112, 1033 (C–O); 860, 840, 785, 717
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (13000),
Schiff bases IIIv and IVm (general procedure).
A solution of 5 mmol bis(4-formyl-2-methoxyphenyl)
succinate or bis(2-ethoxy-4-formylphenyl) succinate
and 10 mmol of cetylamine (II) in 30 ml of anhydrous
methanol was heated for 20 min under reflux. The hot
solution was filtered through a folded filter paper, the
filtrate was cooled and left to stand for 10–15 h at 5°C,
and the precipitate was filtered off through a glass
filter, washed with a small amount of methanol, and
dried in air.
1
220 (13000), 254 (9000), 300 (400). H NMR spec-
trum, δ, ppm: 0.92 t (3H, Me), 1.10–2.00 m (28H,
CH2), 2.32 s (3H, Me), 3.64 t (2H, CH2N), 3.89 s (3H,
MeO), 7.08–7.48 m (3H, Harom), 8.22 s (1H, CH=N).
Found, %: C 74.97; H 10.44; N 3.01. M 408.6.
C26H43NO3. Calculated, %: C 74.78; H 10.38; N 3.35.
M 417.6.
(E)-N-(4-Methoxybenzylidene)hexadecan-1-
amine (IIIa). Yield 89%, mp 30–31°C. IR spectrum, ν,
cm–1: 3075, 3040, 3004 (C–Harom); 2955, 2919, 2850
(C–Haliph); 1646 (C=N); 1606, 1579, 1512 (C=Carom);
1470 (CH2); 1305, 1255, 1164, 1029 (C–O); 860, 832,
820, 770, 722 (δC–Harom). UV spectrum, λmax, nm (ε):
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
propanoate (IIIe). Yield 92%, mp 53–54°C. IR spec-
trum, ν, cm–1: 3070, 3020 (C–Harom); 2956, 2915, 2849
(C–Haliph); 1765 (C=O); 1645 (C=N); 1594, 1514,
1417, 1380 (C=Carom); 1470 (CH2); 1290, 1270, 1209,
1196, 1152, 1111, 1076, 1034 (C–O); 888, 860, 830,
804, 790, 719 (δC–Harom). UV spectrum, λmax, nm (ε):
208 (14000), 220 (13000), 254 (9000), 300 (400).
1H NMR spectrum, δ, ppm: 0.92 t (3H, Me), 1.10–
2.00 m [31H, CH3, CH2), 2.54 q (2H, CH2), 3.64 t (2H,
CH2N), 3.89 s (3H, MeO), 7.08–7.49 m (3H, Harom),
8.22 s (1H, CH=N). Found, %: C 75.61; H 10.58;
1
209 (13000), 221 (12000), 254 (9000). H NMR spec-
trum, δ, ppm: 0.91 t (3H, Me), 1.10–2.05 m (28H,
CH2), 3.55 t (2H, CH2N), 3.87 s (3H, MeO), 6.90–
7.90 m (4H, Harom), 8.17 s (1H, CH=N). Found, %:
C 80.47; H 11.62; N 3.74. M 350.1. C24H41NO. Calcu-
lated, %: C 80.16; H 11.49; N 3.90. M 359.6.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenol
(IIIb). Yield 88%, mp 46–47°C. IR spectrum, ν, cm–1:
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LONG-CHAIN FUNCTIONALLY SUBSTITUTED AROMATIC SCHIFF BASES
1483
N 2.98. M 419.5. C27H45NO3. Calculated, %: C 75.13;
H 10.51; N 3.24. M 431.7.
1204, 1195, 1158, 1113, 1032 (C–O); 860, 830, 780,
718 (δ C–Harom). UV spectrum, λmax, nm (ε): 209
(12000), 220 (13000), 254 (9000), 300 (400). 1H NMR
spectrum, δ, ppm: 0.92 t (6H, Me), 1.10–1.94 m (42H,
(CH2), 2.61 t (2H, CH2), 3.64 t (2H, CH2N), 3.89 s
(3H, MeO), 7.08–7.50 m (3H, Harom), 8.21 s (1H,
CH=N). Found, %: C 77.38; H 11.37; N 2.88. M 506.5.
C34H59NO3. Calculated, %: C 77.07; H 11.22; N 2.64.
M 529.8.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
butanoate (IIIf). Yield 91%, mp 36–37°C. IR spec-
trum, ν, cm–1: 3070, 3010 (C–Harom); 2956, 2915, 2849
(C–Haliph); 1763 (C=O); 1644 (C=N); 1596, 1514,
1416, 1385 (C=Carom); 1472 (CH2); 1290, 1268, 1207,
1150, 1032 (C–O); 872, 840, 785, 754, 716
(δC–Harom). UV spectrum, λmax, nm (ε): 209 (13000),
1
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
octadecanoate (IIIj). Yield 89%, mp 42–43°C. IR
spectrum, ν, cm–1: 3080, 3011 (C–Harom); 2955, 2917,
2850 (C–Haliph); 1751 (C=O); 1647 (C=N); 1600,
1510, 1516, 1380 (C=Carom); 1471 (CH2); 1294, 1274,
1195, 1160, 1143, 1112, 1032 (C–O); 870, 830, 780,
718 (C–Harom). UV spectrum, λmax, nm (ε): 209
(12000), 220 (12000), 254 (8000), 300 (400). 1H NMR
spectrum, δ, ppm: 0.92 t (6H, Me), 1.10–1.96 m (58H,
CH2), 2.62 t (2H, CH2), 3.65 t (2H, CH2N), 3.89 s (3H,
MeO), 7.08–7.54 m (3H, Harom), 8.20 s (1H, CH=N).
Found, %: C 78.93; H 11.96; N 1.80. M 622.3.
C42H75NO3. Calculated, %: C 78.57; H 11.77; N 2.18.
M 642.1.
220 (13000), 254 (9000), 300 (400). H NMR spec-
trum, δ, ppm: 0.91 t (3H, Me), 1.05–2.08 m (33H,
CH3, CH2), 2.55 t (2H, CH2), 3.64 t (2H, CH2N), 3.88 s
(3H, MeO), 7.04–7.52 m (3H, Harom), 8.22 s (1H,
CH=N). Found, %: C 75.92; H 10.76; N 2.81.
M 436.2. C28H47NO3. Calculated, %: C 75.46; H 10.63;
N 3.14. M 445.7.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
2-methylpropanoate (IIIg). Yield 90%, mp 30–31°C.
IR spectrum, ν, cm–1: 3080, 3012 (C–Harom); 2970,
2920, 2850 (C–Haliph); 1764 (C=O); 1647 (C=N);
1600, 1510, 1418, 1385 (C=Carom); 1468 (CH2); 1270,
1200, 1180, 1160, 1124, 1035 (C–O); 866, 821, 780,
752, 721 (δC–Harom). UV spectrum, λmax, nm (ε): 209
(13 000), 220 (13 000), 254 (9000), 300 (400).
1H NMR spectrum, δ, ppm: 0.92 t (3H, Me), 1.24–
1.94 m (34H, Me2C, CH2), 2.83 m (1H, CH), 3.60 t
(2H, CH2N), 3.88 s (3H, MeO), 7.04–7.50 m (3H,
Harom), 8.21 s (1H, CH=N). Found, %: C 75.99;
H 10.70; N 2.84. M 432.6. C28H47NO3. Calculated, %:
C 75.46; H 10.63; N 3.14. M 445.7.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
2-methylprop-2-enoate (IIIk). Yield 88%, mp 36–
37°C. IR spectrum, ν, cm–1: 3075, 3012 (C–Harom);
2960, 2915, 2850 (C–Haliph); 1742 (C=O); 1645
(C=N); 1600, 1590, 1514, 1417, 1385 (C=Carom); 1474
(CH2); 1292, 1265, 1210, 1165, 1132 (CO); 875, 860,
825, 786, 716 (δC–Harom). UV spectrum, λmax, nm (ε):
207 (16000), 220 (16000), 255 (11000), 300 (400).
1H NMR spectrum, δ, ppm: 0.90 t (3H, Me), 1.15–
1.90 m (28H, CH2), 2.00 s (3H, Me), 3.63 t (2H,
CH2N), 3.88 s (3H, MeO), 5.75 m (1H, =CH), 6.40 m
(1H, =CH), 7.10–7.50 m (3H, Harom), 8.22 s (1H,
CH=N). Found, %: C 76.13; H 10.41; N 3.00.
M 425.4. C28H45NO3. Calculated, %: C 75.80; H 10.22;
N 3.16. M 443.7.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
octanoate (IIIh). Yield 93%, mp 33–34°C. IR spec-
trum, ν, cm–1: 3080, 3011 (C–Harom); 2955, 2916, 2850
(C–Haliph); 1762 (C=O); 1647 (C=N); 1598, 1514,
1417, 1380 (C=Carom); 1472 (CH2); 1290, 1200, 1190,
1159, 1112, 1033 (C–O); 865, 830, 780, 720
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (13000),
1
220 (13000), 253 (9000), 300 (400). H NMR spec-
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
phenylacetate (IIIl). Yield 89%, mp 33–34°C. IR
spectrum, ν, cm–1: 3090, 3070, 3034, 3006 (C–Harom);
2954, 2918, 2850 (C–Haliph); 1764 (C=O); 1634
(C=N); 1600, 1557, 1510, 1496, 1432, 1418, 1380
(C=Carom); 1468, 1455 (CH2); 1278, 1235, 1200, 1160,
1120, 1074, 1030 (C–O); 878, 840, 830, 750, 718, 695
(δC–Harom). UV spectrum, λmax, nm (ε): 210 (20000),
trum, δ, ppm: 0.92 t (6H, Me), 1.12–1.90 m (38H,
CH2), 2.62 t (2H, CH2), 3.64 t (2H, CH2N), 3.89 s (3H,
MeO), 7.07–7.50 m (3H, Harom), 8.21 s (1H, CH=N).
Found, %: C 76.90; H 11.14; N 2.50. M 491.0.
C32H55NO3. Calculated, %: C 76.60; H 11.05; N 2.79.
M 501.8.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
decanoate (IIIi). Yield 92%, mp 45–46°C. IR spec-
trum, ν, cm–1: 3075, 3011 (C–Harom); 2955, 2916, 2850
(C–Haliph); 1761 (C=O); 1641 (C=N); 1595, 1540,
1514, 1419, 1379 (C=Carom); 1472 (CH2); 1290, 1270,
1
220 (14000), 256 (10000), 302 (5000). H NMR spec-
trum, δ, ppm: 0.92 t (3H, Me), 1.17–1.90 m (28H,
CH2), 3.65 t (2H, CH2N), 3.82 s (2H, CH2), 3.90 s (3H,
MeO), 7.00–7.54 m (8H, Harom), 8.22 s (1H, CH=N).
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DIKUSAR et al.
1484
Found, %: C 78.08; H 9.76; N 2.58. M 472.0.
C32H47NO3. Calculated, %: C 77.85; H 9.59; N 2.84.
M 493.7.
spectrum, ν, cm–1: 3100, 3080, 3005 (C–Harom); 2955,
2918, 2850 (C–Haliph); 1744 (C=O); 1648 (C=N);
1630, 1592, 1536, 1506, 1484, 1468, 1416, 1398, 1378
(C=Carom); 1468 (CH2); 1274, 1260, 1205, 1160, 1120,
1072, 1034, 1012 (C–O); 875, 848, 814, 748, 720, 684
(δC–Harom). UV spectrum, λmax, nm (ε): 207 (38000),
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
2-phenylbutanoate (IIIm). Yield 91%, mp 35–36°C.
IR spectrum, ν, cm–1: 3090, 3080, 3070, 3040, 3025,
3003 (C–Harom); 2956, 2918, 2850 (C–Haliph); 1758
(C=O); 1646 (C=N); 1600, 1505, 1416, 1383 (C=Carom);
1468, 1454 (CH2); 1270, 1240, 1198, 1152, 1122,
1080, 1038 (C–O); 870, 840, 765, 748, 719, 700
(C–Harom). UV spectrum, λmax, nm (ε): 210 (20000),
1
221 (28000), 256 (24000), 300 (7000). H NMR spec-
trum, δ, ppm: 0.92 t (3H, Me), 1.20–1.98 m (28H,
CH2), 3.65 t (2H, CH2N), 3.89 s (3H, MeO), 7.20–
8.25 m (7H, Harom), 8.25 s (1H, CH=N). Found, %:
C 66.89; H 8.08; Br 13.87; N 2.14. M 542.3.
C31H44BrNO3. Calculated, %: C 66.66; H 7.94;
Br 14.30; N 2.51. M 558.6.
1
220 (14000), 255 (9000), 302 (5000). H NMR spec-
trum, δ, ppm: 0.92 t (3H, Me), 1.18–1.90 m (28H,
CH2), 1.42 d (3H, Me), 2.88 m (2H, CH2), 3.42 m (1H,
CH), 3.66 t (2H, CH2N), 3.90 s (3H, MeO), 7.04–
7.54 m (8H, Harom), 8.22 s (1H, CH=N). Found, %:
C 78.85; H 9.95; N 2.44. M 508.5. C34H51NO3. Calcu-
lated, %: C 78.27; H 9.85; N 2.68. M 521.8.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
3-nitrobenzoate (IIIq). Yield 90%, mp 55–56°C. IR
spectrum, ν, cm–1: 3094, 3080, 3060, 3002 (C–Harom);
2954, 2920, 2850 (C–Haliph); 1750 (C=O); 1647 (C=N);
1634, 1620, 1600, 1505, 1417, 1380 (C=Carom); 1536,
1348 (NO2); 1467 (CH2); 1295, 1275, 1256, 1197,
1160, 1122, 1060, 1032 (C–O); 870, 830, 815, 765,
750, 716 (δC–Harom). UV spectrum, λmax, nm (ε): 204
(36000), 220 (37000), 258 (18000), 302 (7000).
1H NMR spectrum, δ, ppm: 0.92 t (3H, Me), 1.16–
1.96 m (28H, CH2), 3.65 t (2H, CH2N), 3.91 s (3H,
MeO), 7.18–8.44 m (7H, Harom), 8.25 s (1H, CH=N).
Found, %: C 71.28; H 8.66; N 5.11. M 513.2.
C31H44N2O5. Calculated, %: C 70.96; H 8.45; N 5.34.
M 524.7.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
benzoate (IIIn). Yield 90%, mp 34–35°C. IR spec-
trum, ν, cm–1: 3078, 3004 (C–Harom); 2954, 2918, 2850
(C–Haliph); 1756 (C=O); 1647 (C=N); 1600, 1591,
1510, 1437, 1417, 1380 (C=Carom); 1469 (CH2); 1290,
1273, 1243, 1198, 1160, 1112, 1094, 1032 (CO); 870,
815, 785, 744, 720, 706, 680 (δC–Harom). UV spec-
trum, λmax, nm (ε): 207 (33000), 220 (20000), 254
1
(16000), 296 (6000). H NMR spectrum, δ, ppm:
0.92 t (3H, Me), 1.15–1.90 m (28H, CH2), 3.64 t (2H,
CH2N), 3.95 s (3H, MeO), 7.10–8.20 m (8H, Harom),
8.25 s (1H, CH=N). Found, %: C 78.01; H 9.72;
N 2.53. M 465.1. C31H45NO3. Calculated, %: C 77.62;
H 9.45; N 2.92. M 479.7.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
methyl carbonate (IIIr). Yield 91%, mp 44–45°C. IR
spectrum, ν, cm–1: 3068, 3010 (C–Harom); 2955, 2915,
2850 (C–Haliph); 1764 (C=O); 1644 (C=N); 1600, 1598,
1515, 1374 (C=Carom); 1472 (CH2); 1290, 1270, 1225,
1165, 1112, 1032 (C–O); 860, 840, 785, 718
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (12000),
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
2,4-dichlorobenzoate (IIIo). Yield 94%, mp 40–41°C.
IR spectrum, ν, cm–1: 3100, 3085, 3004 (C–Harom);
2960, 2918, 2850 (C–Haliph); 1755 (C=O); 1648
(C=N); 1600, 1586, 1558, 1508, 1417, 1376 (C=Carom);
1468 (CH2); 1275, 1238, 1198, 1160, 1148, 1112,
1087, 1032 (C–O); 870, 830, 804, 785, 760, 720, 680
(δC–Harom). UV spectrum, λmax, nm (ε): 210 (40000),
1
220 (13000), 255 (9000), 300 (400). H NMR spec-
trum, δ, ppm: 0.92 t (3H, Me), 1.10–2.00 m (28H,
CH2), 3.64 t (2H, CH2N), 3.89 (3H, 3-MeO), 3.96 s
(3H, 4-MeOCO), 7.06–7.48 m (3H, Harom), 8.22 s (1H,
CH=N). Found, %: C 72.38; H 10.12; N 2.89.
M 419.7. C26H43NO4. Calculated, %: C 72.02; H 9.99;
N 3.23. M 433.6.
1
223 (30000), 254 (17000), 300 (6000). H NMR spec-
trum, δ, ppm: 0.92 t (3H, Me), 1.18–2.00 m (28H,
CH2), 3.65 t (2H, CH2N), 3.90 s (3H, MeO), 7.10–
8.50 m (6H, Harom), 8.25 s (1H, CH=N). Found, %:
C 68.04; H 8.06; Cl 12.50; N 2.19. M 426.8.
C31H43Cl2NO3. Calculated, %: C 67.87; H 7.90;
Cl 12.93; N 2.55. M 548.6.
Ethyl [(E)-hexadecyliminomethyl]-2-methoxy-
phenyl carbonate (IIIs). Yield 90%, mp 43–44°C. IR
spectrum, ν, cm–1: 3070, 3010 (C–Harom); 2956, 2915,
2850 (C–Haliph); 1765 (C=O); 1644 (C=N); 1601,
1598, 1515, 1374 (C=Carom); 1472 (CH2); 1290, 1272,
1225, 1165, 1112, 1032 (C–O); 860, 840, 785, 718
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (13000),
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
4-bromobenzoate (IIIp). Yield 93%, mp 44–45°C. IR
1
220 (13000), 255 (9000), 300 (400). H NMR spec-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

LONG-CHAIN FUNCTIONALLY SUBSTITUTED AROMATIC SCHIFF BASES
1485
trum, δ, ppm: 0.92 t (3H, Me), 1.10–2.00 m (31H, Me,
CH2), 3.64 t (2H, CH2N), 3.89 (3H, MeO), 4.18 q (2H,
CH2), 7.08–7.48 m (3H, Harom), 8.22 s (1H, CH=N).
Found, %: C 72.56; H 10.31; N 2.80. M 432.6.
C27H45NO4. Calculated, %: C 72.44; H 10.13; N 3.13.
M 447.7.
8.22 s (2H, CH=N). Found, %: C 75.13; H 10.14;
N 3.08. M 814.0. C52H84N2O6. Calculated, %: C 74.96;
H 10.16; N 3.36. M 833.2.
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenol
(IVa). Yield 87%, mp 48–49°C. IR spectrum, ν, cm–1:
3424 (OH); 3070, 3035, 3000 (C–Harom); 2960, 2918,
2850 (C–Haliph); 1643 (C=N); 1588, 1514, 1428, 1355
(C=Carom); 1472 (CH2); 1284, 1235, 1194, 1170, 1128,
1044 (C–O); 870, 824, 760, 720 (δC–Harom). UV spec-
trum, λmax, nm (ε): 208 (10000), 224 (10000), 268
(10000), 302 (6000). 1H NMR spectrum, δ, ppm: 0.92 t
(3H, Me), 1.10–2.00 m (31H, Me, CH2), 3.64 t (2H,
CH2N), 4.10 q (2H, CH2O), 6.70 br.s (1H, OH), 6.98–
7.48 m (3H, Harom), 8.16 s (1H, CH=N). Found, %:
C 77.32; H 11.25; N 3.26. M 368.4. C25H43NO2. Calcu-
lated, %: C 77.07; H 11.12; N 3.59. M 389.6.
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
1,2-dicarba-closo-dodecaborane-1-carboxylate (IIIt).
Yield 88%, mp 40–41°C. IR spectrum, ν, cm–1: 3095,
3066, 3020 (C–Harom, C–Hcarb.); 2956, 2915, 2850
(C–Haliph); 2610, 2580 (B–H); 1770 (C=O); 1646
(C=N); 1594, 1515, 1417, 1380 (C=Carom); 1470 (CH2);
1290, 1270, 1210, 1196, 1152, 1112, 1076, 1034
(C–O); 888, 860, 830, 804, 790, 719 (δC–Harom). UV
spectrum, λmax, nm (ε): 206 (14000), 220 (13000), 254
1
(10000), 300 (400). H NMR spectrum, δ, ppm: 0.92 t
(3H, Me), 1.06–2.00 m (28H, CH2), 3.64 t (2H,
CH2N), 3.89 s (3H, MeO), 4.10 br.s (1H, CHcarb),
7.02–7.58 m (3H, Harom), 8.23 s (1H, CH=N). Found,
%: C 59.90; H 9.65; B 19.28; N 2.14. M 524.9.
C27H51B10NO3. Calculated, %: C 59.41; H 9.42;
B 19.81; N 2.57. M 545.8.
(E)-N-(3-Ethoxy-4-methoxybenzylidene)hexa-
decan-1-amine (IVb). Yield 92%, mp 37–38°C. IR
spectrum, ν, cm–1: 3080, 3004 (C–Harom); 2954, 2916,
2850 (C–Haliph); 1641 (C=N); 1602, 1585, 1514, 1420
(C=Carom); 1471 (CH2); 1265, 1240, 1163, 1137, 1022
(C–O); 872, 811, 740, 718 (δC–Harom). UV spectrum,
λmax, nm (ε): 207 (12000), 225 (11000), 268 (11000),
4-[(E)-Hexadecyliminomethyl]-2-methoxyphenyl
1,3-dicarba-closo-dodecaborane-1-carboxylate
(IIIu). Yield 89%, mp 39–40°C. IR spectrum, ν, cm–1:
3095, 3062, 3020 (C–Harom, C–Hcarb.); 2956, 2914, 2850
(C–Haliph); 2605 (B–H); 1750 (C=O); 1646 (C=N);
1594, 1514, 1417, 1380 (C=Carom); 1471 (CH2); 1290,
1270, 1212, 1196, 1152, 1113, 1076, 1033 (C–O); 886,
860, 830, 804, 790, 718 (δC–Harom). UV spectrum,
λmax, nm (ε): 207 (14000), 220 (13000), 254 (10000),
1
305 (7000). H NMR spectrum, δ, ppm: 0.92 t (3H,
Me), 1.10–2.05 m (31H, Me, CH2), 3.64 t (2H, CH2N),
3.94 s (3H, MeO), 4.26 q (2H, CH2O), 6.90–7.44 m
(3H, Harom), 8.17 s (1H, CH=N). Found, %: C 77.52;
H 11.35; N 3.20. M 390.8. C26H45NO2. Calculated, %:
C 77.37; H 11.24; N 3.47. M 403.6.
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
acetate (IVc). Yield 92%, mp 45–46°C. IR spectrum,
ν, cm–1: 3070, 3016 (C–Harom); 2958, 2918, 2850
(C–Haliph); 1766 (C=O); 1645 (C=N); 1590, 1512,
1434, 1370 (C=Carom); 1468 (CH2); 1286, 1240, 1220,
1194, 1170, 1124, 1040 (C–O); 865, 830, 760, 740,
720 (δ C–Harom). UV spectrum, λmax, nm (ε): 208
1
300 (400). H NMR spectrum, δ, ppm: 0.92 t (3H,
Me), 1.06–2.00 m (28H, CH2), 3.04 br.s (1H, CHcarb),
3.64 t (2H, CH2N), 3.89 s (3H, MeO), 7.02–7.56 m
(3H, Harom), 8.23 s (1H, CH=N). Found, %: C 59.62;
H 9.51; B 19.60; N 2.41. M 532.6. C27H51B10NO3.
Calculated, %: C 59.41; H 9.42; B 19.81; N 2.57.
M 545.8.
1
(12000), 220 (13000), 255 (9000), 301 (4000). H NMR
spectrum, δ, ppm: 0.92 t (3H, Me), 1.10–2.00 m (31H,
Me, CH2), 2.32 s (3H, Me), 3.63 t (2H, CH2N), 4.12 q
(2H, CH2O), 7.08–7.44 m (3H, Harom), 8.22 s (1H,
CH=N). Found, %: C 75.47; H 10.62; N 2.90.
M 421.4. C27H45NO3. Calculated, %: C 75.13; H 10.51;
N 3.24. M 431.7.
Bis{4-[(E)-hexadecyliminomethyl]-2-methoxy-
phenyl} succinate (IIIv). Yield 93%, mp 67–68°C. IR
spectrum, ν, cm–1: 3090, 3070, 3006 (C–Harom); 2956,
2918, 2850 (C–Haliph); 1760 (C=O); 1640 (C=N);
1600, 1540, 1512, 1420, 1378 (C=Carom); 1468 (CH2);
1290, 1272, 1205, 1150, 1124, 1028 (C–O); 870, 830,
785, 720 (δC–Harom). UV spectrum, λmax, nm (ε): 208
(26000), 220 (25000), 255 (17000), 300 (9000).
1H NMR spectrum, δ, ppm: 0.92 t (6H, Me), 1.10–
2.00 m (56H, CH2), 3.04 s (4H, COCH2), 3.64 t (4H,
CH2N), 3.89 s (6H, MeO), 7.08–7.50 m (6H, Harom),
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
propanoate (IVd). Yield 90%, mp 48–49°C. IR spec-
trum, ν, cm–1: 3070, 3056, 3015 (C–Harom); 2958, 2918,
2850 (C–Haliph); 1766 (C=O); 1646 (C=N); 1600, 1594,
1512, 1430, 1380, 1354 (C=Carom); 1468 (CH2); 1284,
1272, 1196, 1164, 1146, 1120, 1080, 1040 (C–O); 890,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

DIKUSAR et al.
1486
840, 802, 760, 740, 720 (δC–Harom). UV spectrum,
λmax, nm (ε): 208 (13000), 220 (14000), 254 (9000),
300 (4000). H NMR spectrum, δ, ppm: 0.92 t (3H,
Me), 1.10–2.00 m (34H, Me, CH2), 2.55 q (2H, CH2),
3.62 t (2H, CH2N), 4.12 q (2H, CH2O), 7.06–7.50 m
(3H, Harom), 8.22 s (1H, CH=N). Found, %: C 75.67;
H 10.74; N 2.84. M 432.9. C28H47NO3. Calculated, %:
C 75.46; H 10.63; N 3.14. M 445.7.
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
4-methylbenzoate (IVh). Yield 94%, mp 32–33°C. IR
spectrum, ν, cm–1: 3090, 3080, 3040, 3005 (C–Harom);
2958, 2918, 2850 (C–Haliph); 1741 (C=O); 1647 (C=N);
1612, 1602, 1510, 1431, 1394, 1380 (C=Carom); 1468
(CH2); 1272, 1201, 1178, 1166, 1119, 1068, 1042,
1020 (C–O); 874, 840, 806, 788, 764, 746, 720
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (35000),
1
1
221 (20000), 254 (24000), 300 (6000). H NMR spec-
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
butanoate (IVe). Yield 89%, mp 38–39°C. IR spec-
trum, ν, cm–1: 3070, 3012 (C–Harom); 2960, 2915, 2850
(C–Haliph); 1767 (C=O); 1646 (C=N); 1600, 1590, 1513,
1431, 1412, 1380 (C=Carom); 1470 (CH2); 1290, 1266,
1154, 1118, 1042 (C–O); 870, 840, 785, 754, 715
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (12000),
trum, δ, ppm: 0.92 t (3H, Me), 1.16–1.92 m (31H, Me,
CH2), 2.45 s (3H, Me), 3.63 t (2H, CH2N), 4.12 q (2H,
CH2O), 7.08–8.14 m (7H, Harom), 8.22 s (1H, CH=N).
Found, %: C 78.25; H 7.74; N 2.38. M 500.1.
C33H49NO3. Calculated, %: C 78.06; H 9.73; N 2.76.
M 507.8.
1
220 (13000), 254 (9000), 300 (4000). H NMR spec-
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
methyl carbonate (IVi). Yield 90%, mp 40–41°C. IR
spectrum, ν, cm–1: 3070, 3010 (C–Harom); 2955, 2915,
2850 (C–Haliph); 1764 (C=O); 1644 (C=N); 1600,
1598, 1515, 1374 (C=Carom); 1472 (CH2); 1290, 1271,
1225, 1165, 1112, 1032 (C–O); 860, 840, 785, 719
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (13000),
trum, δ, ppm: 0.92 t (3H, Me), 1.06–2.08 m (36H, Me,
CH2), 2.54 q (2H, CH2), 3.63 t (2H, CH2N), 4.12 q
(2H, CH2O), 7.06–7.54 m (3H, Harom), 8.22 s (1H,
CH=N). Found, %: C 75.95; H 10.86; N 2.69.
M 444.3. C29H49NO3. Calculated, %: C 75.77; H 10.74;
N 3.05. M 459.7.
1
220 (13000), 255 (9000), 300 (400). H NMR spec-
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
2-methylpropanoate (IVf). Yield 90%, mp 35–36°C.
IR spectrum, ν, cm–1: 3070, 3010 (C–Harom); 2960,
2918, 2850 (C–Haliph); 1764 (C=O); 1647 (C=N); 1600,
1590, 1510, 1432, 1395, 1380 (C=Carom); 1469 (CH2);
1290, 1270, 1205, 1154, 1182, 1167, 1122, 1096, 1044
(C–O); 865, 820, 790, 770, 740, 721 (δC–Harom). UV
spectrum, λmax, nm (ε): 208 (13000), 220 (13000), 255
trum, δ, ppm: 0.92 t (3H, Me), 1.10–2.00 m (31H, Me,
CH2), 3.64 t (2H, CH2N), 3.95 s (3H, MeO), 4.12 q
(2H, CH2), 7.08–7.50 m (3H, Harom), 8.22 s (1H,
CH=N). Found, %: C 72.64; H 10.16; N 2.83.
M 436.5. C27H45NO4. Calculated, %: C 72.44; H 10.13;
N 3.13. M 447.7.
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
ethyl carbonate (IVj). Yield 91%, mp 44–45°C. IR
spectrum, ν, cm–1: 3070, 3010 (C–Harom); 2956, 2915,
2850 (C–Haliph); 1765 (C=O); 1644 (C=N); 1600, 1597,
1515, 1374 (C=Carom); 1471 (CH2); 1290, 1271, 1224,
1165, 1112, 1032 (C–O); 860, 840, 784, 719
(δC–Harom). UV spectrum, λmax, nm (ε): 208 (12000),
1
(9000), 300 (4000). H NMR spectrum, δ, ppm: 0.92 t
(3H, Me), 1.14–1.90 m (37H, Me, Me2C, CH2), 2.80 m
(1H, CH), 3.62 t (2H, CH2N), 4.12 q (2H, CH2O),
7.02–7.50 m (3H, Harom), 8.22 s (1H, CH=N). Found,
%: C 75.98; H 10.89; N 2.87. M 448.7. C29H49NO3.
Calculated, %: C 75.77; H 10.74; N 3.05. M 459.7.
1
220 (13000), 255 (9000), 300 (400). H NMR spec-
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
3-methylbutanoate (IVg). Yield 93%, mp 32–33°C.
IR spectrum, ν, cm–1: 3070, 3040, 3016 (C–Harom);
2958, 2918, 2851 (C–Haliph); 1764 (C–Haliph); 1648
(C=N); 1600, 1595, 1510, 1431, 1395, 1380 (C=Carom);
1468 (CH2); 1289, 1272, 1195, 1164, 1120, 1043
(C–O); 870, 825, 795, 760, 740, 721 (δC–Harom). UV
spectrum, λmax, nm (ε): 208 (12000), 220 (13000), 254
trum, δ, ppm: 0.92 t (3H, Me), 1.10–2.00 m (34H, Me,
CH2), 3.64 t (2H, CH2N), 3.90–4.20 m (4H, CH2),
7.08–7.52 m (3H, Harom), 8.22 s (1H, CH=N). Found,
%: C 73.12; H 10.38; N 2.74. M 449.4. C28H47NO4.
Calculated, %: C 72.84; H 10.26; N 3.03. M 461.7.
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
1,2-dicarba-closo-dodecaborane-1-carboxylate
(IVk). Yield 87%, mp 30–31°C. IR spectrum, ν, cm–1:
3095, 3067, 3020 (C–Harom, C–Hcarb); 2954, 2915, 2850
(C–Haliph); 2611, 2580 (B–H); 1770 (C=O); 1646
(C=N); 1594, 1514, 1417, 1380 (C=Carom); 1471 (CH2);
1290, 1270, 1210, 1196, 1151, 1112, 1076, 1032
(C–O); 888, 860, 831, 804, 790, 718 (δC–Harom). UV
1
(9000), 300 (4000). H NMR spectrum, δ, ppm: 0.92 t
(3H, Me), 1.08 d (6H, Me2C), 1.12–2.82 m (34H, Me,
CH, CH2), 3.62 t (2H, CH2N), 4.12 q (2H, CH2O),
7.02–7.46 m (3H, Harom), 8.22 s (1H, CH=N). Found,
%: C 76.27; H 10.92; N 2.60. M 458.2. C30H51NO3.
Calculated, %: C 76.06; H 10.85; N 2.96. M 473.7.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

LONG-CHAIN FUNCTIONALLY SUBSTITUTED AROMATIC SCHIFF BASES
1487
spectrum, λmax, nm (ε): 206 (14000), 220 (13000), 254
(10000), 300 (400). H NMR spectrum, δ, ppm: 0.92 t
This study was performed under financial support
by the Byelorussian Republican Foundation for Basic
Research (project no. Kh08-227).
1
(3H, Me), 1.06–2.00 m (31H, Me, CH2), 3.64 t (2H,
CH2N), 4.08 br.s (1H, CHcarb), 4.12 q (2H, CH2O),
7.02–7.54 m (3H, Harom), 8.23 s (1H, CH=N). Found,
%: C 60.31; H 9.87; B 19.10; N 2.18. M 542.7.
C28H53B10NO3. Calculated, %: C 60.07; H 9.54;
B 19.31; N 2.50. M 559.8.
REFERENCES
1. Dikusar, E.A., Potkin, V.I., Kozlov, N.G., and Yuvchen-
ko, A.P., Russ. J. Gen. Chem., 2006, vol. 76, p. 1425.
2. Azarko, V.A., Dikusar, E.A., Potkin, V.I., Kozlov, N.G.,
and Yuvchenko, A.P., Optika neodnorodnykh struktur –
2007: materialy mezhdunarodnoi nauchno-praktiche-
skoi konferentsii (Optics of Heterogeneous Structures
2007. Proc. Int. Scientific and Practical Conf.),
Mogilev: Mogilev. Gos. Univ. imeni A.A. Kuleshova,
2007, p. 27.
3. Zhavnerko, G.K., Supichenko, G.N., Agabekov, V.E.,
Moiseichuk, K.L., Dikusar, E.A., Gallyamov, M.O., and
Yaminskii, I.V., Zh. Fiz. Khim., 2002, vol. 76, p. 1634.
4. Abramzon, A.A., Poverkhnostno-aktivnye veshchestva.
Svoistva i primenenie (Surfactants. Properties and Ap-
plication), Leningrad: Khimiya, 1981, p. 304.
5. Dyer, J.R., Applications of Absorption Spectroscopy of
Organic Compounds, Englewood Cliffs: Prentice–Hall,
1965. Translated under the title Prilozheniya absorbtsi-
2-Ethoxy-4-[(E)-hexadecyliminomethyl]phenyl
1,3-dicarba-closo-dodecaborane-1-carboxylate
(IVl). Yield 89%, mp 30–31°C. IR spectrum, ν, cm–1:
3095, 3066, 3020 (C–Harom, C–Hcarb); 2955, 2915, 2850
(C–Haliph); 2605 (B–H); 1750 (C=O); 1646 (C=N);
1594, 1514, 1417, 1380 (C=Carom); 1472 (CH2); 1290,
1270, 1212, 1196, 1151, 1113, 1076, 1032 (C–O); 886,
860, 830, 805, 790, 718 (δC–Harom). UV spectrum,
λ
max, nm (ε): 205 (14000), 220 (13000), 255 (10000),
1
300 (400). H NMR spectrum, δ, ppm: 0.92 t (3H,
Me), 1.06–2.02 m (31H, Me, CH2), 3.04 br.s (1H,
CHcarb), 3.64 t (2H, CH2N), 4.12 q (2H, CH2O), 7.02–
7.56 m (3H, Harom), 8.23 s (1H, CH=N). Found, %:
C 60.24; H 10.10; B 19.08; N 2.35. M 547.2.
C28H53B10NO3. Calculated, %: C 60.07; H 9.54;
B 19.31; N 2.50. M 559.8.
onnoi
spektroskopii
organicheskikh
soedinenii,
Moscow: Khimiya, 1970, p. 92.
Bis{2-ethoxy-4-[(E)-hexadecyliminomethyl]-
phenyl} succinate (IVm). Yield 91%, mp 60–61°C. IR
spectrum, ν, cm–1: 3070, 3058, 3010 (C–Harom); 2955,
2918, 2850 (C–Haliph); 1763 (C=O); 1646 (C=N); 1600,
1594, 1548, 1510, 1431, 1394, 1380 (C=Carom); 1470
(CH2); 1287, 1273, 1201, 1166, 1120, 1041 (C–O);
870, 834, 801, 760, 740, 721 (δC–Harom). UV spec-
trum, λmax, nm (ε): 207 (25000), 220 (25000), 255
6. Dikusar, E.A., Vyglazov, O.G., Moiseichuk, K.L.,
Zhukovskaya, N.A., and Kozlov, N.G., Zh. Prikl. Khim.,
2005, vol. 78, p. 122.
7. Dikusar, E.A. and Kozlov, N.G., Khim. Prirodn. Soedin.,
2005, p. 74.
8. Dikusar, E.A. and Kozlov, N.G., Russ. J. Org. Chem.,
2005, vol. 41, p. 992.
9. Dikusar, E.A., Zh. Prikl. Khim., 2006, vol. 79, p. 1043.
10. Dikusar, E.A., Kozlov, N.G., Potkin, V.I., Zvereva, T.D.,
Yuvchenko, A.P., Bei, M.P., and Kovganko, N.V., Khim.
Prirodn. Soedin., 2006, p. 434.
11. Dikusar, E.A., Potkin, V.I., Kozlov, N.G., Yuvchen-
ko, A.P., Bei, M.P., and Kovganko, N.V., Russ. J. Org.
Chem., 2008, vol. 44, p. 1305.
1
(19000), 300 (8000). H NMR spectrum, δ, ppm:
0.92 t (6H, Me), 1.12–1.96 (62H, Me, CH2), 3.03 s
(4H, CH2CO), 3.63 t (4H, CH2N), 4.12 q (4H, CH2O),
7.10–7.45 m (6H, Harom), 8.22 s (2H, CH=N). Found,
%: C 75.46; H 10.38; N 3.02. M 843.5. C54H88N2O6.
Calculated, %: C 75.30; H 10.32; N 3.25. M 861.3.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009