Functionalyzed nitrogen- and phosphorus-containing salts of cycloalkanecarboxylic and carboranecarboxylic acids

Article abstract of DOI:10.1007/s11176-005-0173-6

A highly selective method for preparing potentially biologically active functionalyzed substituted nitrogen-and phosphorus-containing salts of maleopimaric, o(m)-carborane-1-carboxylic, D,L-camphoric, and m-carborane-1,7-dicarboxylic acids is developed.

Full text of DOI:10.1007/s11176-005-0173-6

Russian Journal of General Chemistry, Vol. 75, No. 1, 2005, pp. 58 68. Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 1, 2005, pp. 67 76.
Original Russian Text Copyright 2005 by Dikusar, Kozlov, Zvereva, Murashko, Yuvchenko, Bey, Ol’khovik.
Functionalyzed Nitrogen- and Phosphorus-containing Salts
of Cycloalkanecarboxylic and Carboranecarboxylic Acids
E. A. Dikusar, N. G. Kozlov, T. D. Zvereva, V. L. Murashko,
A. P. Yuvchenko, M. P. Bey, and V. K. Ol’khovik
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 March 25, 2003
Abstract A highly selective method for preparing potentially biologically active functionalyzed substituted
nitrogen- and phosphorus-containing salts of maleopimaric, o(m)-carborane-1-carboxylic, D,L-camphoric, and
m-carborane-1,7-dicarboxylic acids is developed.
The interest in functionalyzed nitrogen- and phos-
phorus-containing salts of carboxylic acids is caused
by the broad range of their useful properties, such as
a high biological [1 5] and adhesive activity [6 8].
thesis of carborane derivatives, including nitrogen-
and phosphorus-containing [24 32].
The aim of this work was to develop a highly ef-
fective synthetic route to the potentially biologically
active functionalyzed nitrogen- and phosphorus-con-
taining salts of acids Ia Ie. Previously unknown salts
IIIa IIIt, IVa IVi, Va Vi, and VIIa VIIi were
prepared by the reactions of acids Ia Ie with aliphatic,
aromatic, or heterocyclic amines and triphenylphos-
phine (II) (1:1 or 1:2 acid:II ratios with acids Ia
Ic and Id, Ie, respectively) in absolute chloroform (for
IIIa IIIt, IVa IVi, Va Vi) or methanol (for VIa VIi,
VIIa VIIi). The reaction was complete within 10 15
min at 20 23 C. The yields of salts IIIa IIIt, IVa
IVi, Va Vi, and VIIa VIIi were 89 96%.
The choice of maleopimaric Ia, o- and m-carbo-
rane-1-carboxylic (Ib, Ic), D,L-camphoric (1,2,2-trime-
thylcyclopentane-1,3-dicarboxylic) (Id), and m-carbo-
rane-1,7-dicarboxylic acids (Id) was motivated by the
similarity of their spatial arrangement and the ne-
cessity of comparative study of the biological activity
associated with pharmacophoric molecular fragments
bound with the carboxy and amino groups.
Maleopimaric acid (Ia) is a dienic adduct prepared
from levopimaric acid and maleic anhydride by the
Diels Alder reaction [9 11]. Acid Ia is a convenient
and easily available synthon for preparing compounds
possessing a broad-spectrum biological, specifically
antiphlogistic, nematocide, and fungicide, activity
[12 17], as well as monomers [18, 19]. The high bi-
ological activity of derivatives of maleopimaric acid
(Ia) is explained by the stereochemical similarity of
their 13 configuration to the A, B, and C rings of
steroids [10, 20].
The resulting salts are colorless or slightly colored
brittle crystalline substances. They are readily soluble
in acetone and C1 C4 alcohols and poorly soluble in
water. All the salts are nonhygroscopic and withstand
handling in sealed ampules at 0 5 C in the dark.
The structures of acids Ia Ie and salts IIIa IIIt,
Va Vi, VIa VIi, and VIIa VIIi were confirmed by
1
their elemental analyses and H NMR, IR, and UV
spectra (Tables 1 3) [33, 34].
Boron compounds have first been applied for boron
neutron capture therapy of cancer 1936 [21]. It is a
binary radiotherapy that involves capture of heat
neutrons by 10B nuclei and their selective transfer to
cancer cells. The neutron capture produces an excited
11B nucleus that is then split to form two high-energy
Thermal stability of peroxy derivatives VIg and
VIIg was assessed by means of thermal analysis.
Analysis of the DTG, TG, and DTA curves show that
peroxides VIg and VIg are fairly thermally stable
compounds. Peroxide VIh derived from D,L-cam-
phoric acid (Id) and a peroxy-containing amine begins
to decompose at an appreciable and a well-defined
heat release at 142 C (first stage of decomposition:
142 212 C, maximum 182 C, weight loss 24.5%).
Compound VIIg derived from m-carborane-1,7-di-
7
4He2+ and Li3+ ions. These charged species create
ionized tracks along their trajectories, thus causing
cell decay [5, 22, 23]. One of the promising directions
in the search for objects for preparing boron clusters
for use in diagnostics and therapy of cancer is syn-
1070-3632/05/7501-0058 2005 Pleiades Publishing, Inc.

FUNCTIONALYZED NITROGEN- AND PHOSPHORUS-CONTAINING SALTS
59
NR
II
RCOOH
RCOOH NR
Ia Ic
IIIa IIIt, IVa IVi,
Va Vi
O
OH NR
O
R
OH
NR
II
R
OH NR
OH
O
O
Id, Ie
VIa VIi, VIIa VIIi
18
7
19
8
20
6
17
12
16
4
3
5
O
21
RCOOH =
(Ia, III), o-HCB10H10CCOOH (Ib, IV), m-HCB10H10CCOOH (Ic, V);
13
2
1
14
O
HOOC
22
11 10
9
O
3
2
R (COOH)2 =
HO
(Id, VI), m-HOOCB10H10CCOOH (Ie, VII); II, III, NR = NH2Me (a), NHMe2 (b),
1
OH
5
4
O
O
H2N
(d), NH2C6H5 (e), NH(CH2C6H5)2 (f), NH2C6H4Me-m (g), NH2C6H4-p (h),
NEt3 (c),
O
MeO
O
NH2C6H4OH-o (i), Me2NC6H4CHO-p (j), Et2NC6H4CHO-p (k),
(l),
(m),
NH2
OMe
NH2
(r),
H
H
N
N
|
.
(p),
O
(o),
(q),
HN
(n), HN
(s), P(C6H5)3 (t), II, IV, V,
N
N
N
O
OH
H
N
|
.
(e),
(f),
(g),
NR = NEt3 (a), NH2C6H4OH-o (b), Me2NC6H4CHO-p (c), HN
(d),
N
O
HO
H
N
O
MeO
NR = NH C H OH-o (a), Me NC H CHO-p (b),
(h), P(C6H5)3 (i), II, VI, VII,
N
2
6
4
2
6
4
O
OMe
N
NH2
H
N
H
|
.
N
|
.
(c),
(d),
(e),
NH2
(f),
(g),
(h),
P(C6H5)3 (i).
N
HO
NH2
O
OH
O O
carboxylic acid (Id) is slightly more stable thermally
than peroxide VIg and decomposes at 150 C (first
stage of decomposition: 150 205 C, maximum 185 C,
weight loss 38.5%).
EXPERIMENTAL
The IR spectra were recorded on a Protege-460
Fourier spectrometer in KBr pellets. The H NMR
spectra were measured on a Tesla 567A spectrometer
(100 MHz) in CDCl3 (Ia Ic, IIIa IIIt, IVa, IVc, IVd,
IVf, IVh, Va, Vc Vf, Vh, and Vi) or (CD3)2CO (Id,
1
The purity of the products was 99 1% (NMR
data) [33].
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005

60
Table 1. Properties of compounds Ia Ie, IIIa IIIt, IVa IVi, Va Vi, VIa VIi, and VIIa VIIi
Found, % Calculated, %
DIKUSAR et al.
Comp. Yield, mp,
C
Formula
Mcalc
no.
%
(decomp.)
C
H
B (Br) N (P)
C
H
B (Br) N (P)
Ia
Ib
Ic
Id
225
150
163
185
203
67
130
86
158
63
59
64
56
116
36
31
157
75
77
146
57
118
47
68
47
86
204
104
197
185
156
167
107
54
103
187
103
201
112
161
131
84
72.16
19.35
19.40
60.38
20.87
69.74
70.29
72.04
72.35
73.12
76.51
73.52
63.11
71.03
72.34
72.90
70.33
75.40
71.88
69.19
72.13
72.71
72.73
69.61
76.29
37.59
36.49
42.82
35.29
44.11
36.07
43.52
35.51
56.12
37.61
36.47
42.93
35.32
44.19
36.12
43.44
35.41
56.20
63.36
67.62
65.63
74.28
74.31
7.91
6.56
6.54
8.18
5.32
8.77
9.01
9.56
9.22
8.14
8.05
8.25
6.84
7.94
8.03
8.32
7.11
7.73
9.04
8.74
8.91
7.84
7.34
7.34
7.25
9.57
6.52
6.92
8.73
8.34
6.54
5.83
5.72
6.15
9.55
6.56
7.02
8.65
8.35
6.56
5.91
5.65
6.27
7.41
7.93
6.18
7.17
7.25
C24H32O5
C3H12B10O2
C3H12B10O2
C10H16O4
C4H12B10O4
71.97
19.14
19.14
59.98
20.69
69.58
70.08
71.82
72.11
72.99
76.35
73.34
62.94
70.70
72.10
72.76
70.05
75.11
71.72
68.97
71.93
72.62
72.64
69.34
76.11
37.35
36.35
42.71
35.15
43.92
35.94
43.23
35.17
55.99
37.35
36.35
42.71
35.15
43.92
35.94
43.23
35.17
55.99
63.14
67.45
65.44
74.05
74.05
8.05
6.43
6.43
8.05
5.21
8.64
8.82
9.44
9.08
7.96
7.92
8.14
6.69
7.71
7.88
8.20
6.91
7.60
8.92
8.47
8.70
7.78
7.20
7.18
7.15
9.40
6.44
6.87
8.48
8.22
6.41
5.74
5.57
6.04
9.40
6.44
6.87
8.48
8.22
6.41
5.74
5.57
6.04
7.23
7.68
6.01
7.04
7.04
400.5
188.2
188.2
200.2
232.3
431.6
445.6
501.7
499.7
493.6
597.8
507.7
572.5
509.6
549.7
577.8
685.8
543.7
485.7
487.6
567.8
479.6
545.7
519.6
662.8
289.4
297.4
337.4
273.4
355.5
276.3
333.4
57.21
57.30
57.43
57.43
Ie
46.16
13.80
46.55
13.96
IIIa
IIIb
IIIc
IIId
IIIe
IIIf
IIIg
IIIh
IIIi
IIIj
IIIk
IIIl
IIIm
IIIn
IIIo
IIIp
IIIq
IIIr
IIIs
IIIt
IVa
IVb
IVc
IVd
IVe
IVf
IVg
IVh
IVi
Va
Vb
Vc
Vd
Ve
Vf
Vg
Vh
Vi
VIa
VIb
VIc
VId
VIe
96
90
95
92
93
95
90
92
91
94
93
94
96
91
92
95
94
94
91
96
89
97
95
93
94
94
93
90
91
95
96
94
96
92
93
95
95
92
95
94
94
93
96
3.16 C25H37NO5
2.99 C26H39NO5
2.64 C30H47NO5
2.64 C30H45NO5
2.65 C30H39NO5
2.19 C38H47NO5
2.50 C31H41NO5
2.22 C30H38BrNO5
2.56 C30H39NO6
2.27 C33H43NO6
2.19 C35H47NO6
1.96 C40H47NO9
2.32 C34H41NO5
2.60 C29H43NO5
2.56 C28H41NO6
2.31 C34H49NO6
2.80 C29H37NO5
2.40 C33H39NO6
7.91 C30H37N3O5
4.60 C42H47PO5
4.50 C9H27B10NO2
4.41 C9H19B10NO3
4.08 C12H23B10NO3
5.01 C8H23B10NO2
3.80 C13H29B10NO3
5.08 C8H17B10NO2
4.07 C12H19B10NO3
3.25
3.14
2.79
2.80
2.84
2.34
2.76
2.45
2.75
2.55
2.42
2.04
2.58
2.88
2.87
2.47
2.92
2.57
8.09
4.67
4.84
4.71
4.15
5.12
3.94
5.24
4.20
37.51
36.11
31.91
39.39
30.28
40.19
32.22
37.35
36.36
32.04
39.55
30.41
40.44
32.43
35.01 13.21 C9H17B10N3O2
30.48 C21H27B10PO2
35.17 13.67 307.4
24.00
37.35
36.36
32.04
39.55
30.41
40.44
32.43
6.87
4.84
4.71
4.15
5.12
3.94
5.24
4.20
450.5
289.4
297.4
337.4
273.4
355.5
276.3
333.4
37.20
36.20
31.88
39.37
30.12
40.21
33.22
4.60 C9H27B10NO2
4.55 C9H19B10NO3
4.01 C12H23B10NO3
5.10 C8H23B10NO2
3.70 C13H29B10NO3
5.10 C8H17B10NO2
4.06 C12H19B10NO3
34.98 13.25 C9H17B10N3O2
30.39 C21H27B10PO2
35.17 13.67 307.4
53
153
58
157
39
103
24.00
6.87
6.69
5.62
3.63
5.76
5.76
450.5
418.5
498.6
770.8
486.6
486.6
6.48 C22H30N2O6
5.39 C28H38N2O6
3.30 C42H46N2O12
5.38 C30H34N2O4
5.41 C30H34N2O4
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005

FUNCTIONALYZED NITROGEN- AND PHOSPHORUS-CONTAINING SALTS
61
Table 1. (Contd.)
Found, %
Calculated, %
Comp. Yield, mp,
C
Formula
Mcalc
no.
%
(decomp.)
C
H
B (Br) N (P)
C
H
B (Br) N (P)
VIf
VIg
VIh
VIi
VIIa
VIIb
VIIc
VIId
VIIe
VIIf
VIIg
VIIh
VIIi
94
92
94
94
96
92
95
94
95
96
93
96
93
42
83
69
67.62
68.29 10.03
9.63
5.22 C30H50N2O6
3.18 C48H82N2O10
5.44 C28H30N2O6
8.39 C46H46P2O4
5.98 C16H26B10N2O6 42.66
5.11 C22H34B10N2O6 49.80
3.25 C36H42B10N2O12 53.86
5.18 C24H30B10N2O4 55.58
5.19 C24H30B10N2O4 55.58
4.87 C24H46B10N2O6 50.86
2.99 C42H78B10N2O10 57.38
5.17 C22H26B10N2O6 50.57
67.38
68.05
68.56
76.23
9.42
9.76
6.16
6.40
5.82
6.46
5.27
5.83
5.83
8.18
8.94
5.01
5.59
5.24
3.31
5.71
8.55
6.22
5.28
3.49
5.40
5.40
4.94
3.19
5.36
8.19
534.7
847.2
490.6
724.8
450.5
530.6
802.8
518.6
518.6
566.8
879.2
522.6
756.8
68.90
76.20
42.84
50.11
54.06
55.81
55.77
51.09
57.52
50.74
63.81
6.31
6.51
6.01
6.58
5.42
6.02
5.96
8.31
9.10
5.13
5.71
64
206
108
138
84
105
198
106
71
23.89
20.09
13.10
20.63
20.73
18.89
12.09
20.48
24.00
20.37
13.47
20.85
20.85
19.08
12.30
20.69
14.29
63
22.20
C40H42B10P2O4
63.48
Table 2. 1H NMR spectra of compounds Ia Ie, IIIa IIIt, IVa IVi, Va Vi, VIa VIi, and VIIa VIIi
Comp.
, ppm
no.
Ia
0.57 s (3H, C12Me), 0.97 d (6H, Me2C), 1.14 s (3H, C1Me), 0.80 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.49 s (1H, C=CH), 5.50 6.90 br.s (1H, COOH)
Ib
1.80 7.00 m (10H, B10H10), 4.05 s (1H, CH), 10.22 s (1H, COOH)
Ic
1.45 6.80 m (10H, B10H10), 3.04 s (1H, CH), 8.98 s (1H, COOH)
Id
Ie
IIIa
0.89 s (3H, Me), 1.25 s and 1.32 s (6H, Me2), 1.40 3.10 m [5H, CH and (CH2)2], 10.15 br.s (2H, 2COOH)
1.50 8.00 m (10H, B10H10), 7.00 br.s (2H, 2COOH)
0.56 s (3H, C12Me), 0.96 d (6H, Me2C), 1.11 s (3H, C1Me), 0.80 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
2.52 s (3H, MeN), 5.48 s (1H, C=CH), 8.55 9.05 br.s (3H, NH3)
IIIb
IIIc
IIId
IIIe
IIIf
IIIg
IIIh
IIIi
0.57 s (3H, C12Me), 0.95 d (6H, Me2C), 1.09 s (3H, C1Me), 0.75 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
2.50 s (6H, Me2N), 5.46 s (1H, C=CH), 9.18 br.s (2H, NH2)
0.56 s (3H, C12Me), 0.96 d (6H, Me2C), 1.05 t (9H, 3MeCH2), 1.10 s (3H, C1Me), 0.70 3.05 m [24H, 6CH,
4CH2, (CH2)2 and (CH2)3], 5.46 s (1H, C=CH), 10.28 br.s (1H, NH)
0.57 s (3H, C12Me), 1.02 d (6H, Me2C), 1.20 s (3H, C1Me), 0.75 3.20 m [29H, 7CH, CH2, (CH2)2, (CH2)3 and
(CH2)5], 5.47 s (1H, C=CH), 7.00 8.50 br.s (3H, NH3)
0.56 s (3H, C12Me), 0.95 d (6H, Me2C), 1.12 s (3H, C1Me), 0.80 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 6.00 br.s (3H, NH3), 6.50 7.35 m (5H, C6H5)
0.55 s (3H, C12Me), 0.94 d (6H, Me2C), 1.10 s (3H, C1Me), 0.85 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
3.84 s [4H, N(CH2)2], 5.48 s (1H, C=CH), 6.80 7.90 br.s (2H, NH2), 7.10 7.40 m (10H, 2C6H5)
0.56 s (3H, C12Me), 0.94 d (6H, Me2C), 1.13 s (3H, C1Me), 0.80 3.25 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
2.22 s (3H, MeC6H4), 5.34 br.s (3H, NH3), 5.49 s (1H, C=CH), 6.30 7.10 m (4H, C6H4)
0.56 s (3H, C12Me), 0.95 d (6H, Me2C), 1.13 s (3H, C1Me), 0.75 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.05 br.s (3H, NH3), 5.48 s (1H, C=CH), 6.30 7.40 m (4H, C6H4)
0.56 s (3H, C12Me), 0.95 d (6H, Me2C), 1.13 s (3H, C1Me), 0.75 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
0.48 s (1H, C=CH), 6.40 7.70 m (4H, NH3 and OH), 6.95 7.40 m (4H, C6H4)
0.57 s (3H, C12Me), 0.95 d (6H, Me2C), 1.14 s (3H, C1Me), 0.75 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
3.04 s (6H, Me2N), 5.48 s (1H, C=CH), 6.45 7.85 m (4H, C6H4), 9.69 s (1H, CHO)
0.57 s (3H, C12Me), 0.96 s (6H, Me2C), 1.14 s (3H, C1Me), 1.17 t (6H, 2MeCH2), 0.70 3.20 m [18H, 6CH, CH2,
(CH2)2 and (CH2)3], 3.42 q [4H, N(CH2)2], 5.48 s (1H, C=CH), 6.45 7.85 m (4H, C6H4), 9.65 s (1H, CHO)
IIIj
IIIk
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005

62
DIKUSAR et al.
Table 2. (Contd.)
Comp.
no.
, ppm
IIIl
0.57 s (3H, C12Me), 0.96 d (6H, Me2C), 1.14 s (3H, C1Me), 0.80 3.15 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
3.87 s and 3.91 s (6H, 2COOMe), 5.48 s (1H, C=CH), 6.95 8.20 m (10H, C6H4, C6H3 and NH3)
0.55 s (3H, C12Me), 0.94 d (6H, Me2), 1.13 s (3H, C1Me), 0.75 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 5.75 br.s (3H, NH3), 6.75 7.80 m (7H, C10H7)
IIIm
IIIn
IIIo
IIIp
IIIq
IIIr
IIIs
IIIt
0.55 s (3H, C12Me), 0.96 d (6H, Me2C), 1.07 s (3H, C1Me), 0.70 3.75 m [28H, 6CH, CH2, (CH2)2, (CH2)3 and
(CH2)5], 5.48 s (1H, C=CH), 7.40 8.50 m (2H, NH2)
0.56 s (3H, C12Me), 0.96 d (6H, Me2C), 1.10 s (3H, C1Me), 0.70 4.00 m [26H, 6CH, CH2, 3(CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 8.35 br.s (2H, NH2)
0.56 s (3H, C12Me), 0.97 d (6H, Me2C), 1.11 s (3H, C1Me), 1.22 d (3H, MeCH), 0.70 3.30 m [31H, 9CH, 2CH2,
(CH2)2, (CH2)3 and (CH2)4], 5.48 s (1H, C=CH), 5.75 7.00 br.s (2H, NH2)
0.57 s (3H, C12Me), 0.95 d (6H, Me2C), 1.15 s (3H, C1Me), 0.75 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 7.15 8.85 m (5H, C5H5N), 10.17 br.s (1H, NH)
0.57 s (3H, C12Me), 0.95 d (6H, Me2C), 1.14 s (3H, C1Me), 0.75 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 7.05 8.85 m (8H, C9H6N, NH and OH)
0.57 s (3H, C12Me), 0.94 d (6H, Me2C), 1.15 s (3H, C1Me), 0.75 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 7.20 8.00 m (4H, C6H4), 7.70 9.00 br.s (2H, NH2)
0.56 s (3H, C12Me), 0.96 d (6H, Me2C), 1.13 s (3H, C1Me), 0.75 3.20 m [18H, 6CH, CH2, (CH2)2 and (CH2)3],
5.48 s (1H, C=CH), 7.00 7.50 m (15H, 3C6H5), 7.65 br.s (1H, PH)
IVa
IVb
IVc
1.40 5.80 m (10H, B10H10), 1.29 t (9H, 3Me), 3.06 q (6H, 3CH2), 4.10 s (1H, CH), 10.30 br.s (1H, NH)
1.40 5.80 m (10H, B10H10), 4.45 s (1H, CH), 6.35 7.15 m (4H, C6H4)
1.50 6.20 m (10H, B10H10), 3.13 s (6H, Me2N), 4.10 s (1H, CH), 6.65 7.95 m (4H, C6H4), 9.55 s (1H, CHO),
10.74 s (1H, NH)
IVd
IVe
IVf
IVg
IVh
IVi
Va
1.80 6.20 m (10H, B10H10), 1.45 3.15 m [10H, (CH2)5], 4.08 s (1H, CH), 7.55 br.s (2H, NH2)
1.60 6.50 m (10H, B10H10), 1.00 4.60 m [14H, 4CH, CH2 and (CH2)4], 1.42 d (3H, Me)
1.60 6.20 m (10H, B10H10), 4.17 s (1H, CH), 7.70 9.12 m (5H, C5H5N), 17.03 s (1H, NH)
1.70 6.20 m (10H, B10H10), 4.50 s (1H, CH), 7.20 9.01 m (6H, C9H6N)
1.50 5.90 m (10H, B10H10), 4.15 s (1H, CH), 7.15 8.10 m (4H, C6H4), 13.58 s (2H, NH2)
1.40 5.80 m (10H, B10H10), 3.95 s (1H, CH), 7.00 7.70 m (15H, 3C6H5), 10.30 s (1H, PH)
1.40 5.80 m (10H, B10H10), 1.26 t (9H, 3Me), 3.00 s (1H, CH), 3.05 q (6H, 3CH2), 12.60 br.s (1H, NH)
1.40 6.00 m (10H, B10H10), 3.65 s (1H, CH), 6.45 7.30 m (4H, C6H4)
Vb
Vc
1.35 5.80 m (10H, B10H10), 3.01 s (1H, CH), 3.11 s (6H, Me2N), 6.55 7.80 m (4H, C6H4), 9.20 s (1H, NH),
9.64 s (1H, CHO)
Vd
Ve
Vf
Vg
Vh
Vi
1.40 6.40 m (10H, B10H10), 1.40 3.40 m [11H, CH and (CH2)5], 9.05 br.s (2H, NH2)
1.40 5.90 m (10H, B10H10), 1.00 3.65 m [14H, 4CH, CH2 and (CH2)4], 1.31 d (3H, Me), 8.65 br.s (2H, NH2)
1.40 5.80 m (10H, B10H10), 2.98 s (1H, CH), 7.50 8.80 m (5H, C5H5N), 11.57 s (1H, NH)
1.60 6.80 m (10H, B10H10), 3.78 s (1H, CH), 7.00 8.95 m (6H, C9H6N)
1.40 6.80 m (10H, B10H10), 3.04 s (1H, CH), 7.10 8.10 m (4H, C6H4), 12.85 s (2H, NH2)
1.40 6.80 m (10H, B10H10), 2.95 s (1H, CH), 7.15 7.40 m (15H, 3C6H5), 9.55 s (1H, PH)
0.89 s (3H, Me), 1.25 s and 1.32 s (6H, Me2C), 1.40 3.10 m [5H, CH and (CH2)2], 5.80 br.s (2H, 2OH), 6.30
7.00 m (14H, 2NH3 and 2C6H4)
VIa
VIb
VIc
VId
VIe
0.89 s (3H, Me), 1.25 s and 1.32 s (6H, Me2C), 1.40 3.10 m [5H, CH and (CH2)2], 3.09 s (12H, 2Me2N), 6.70
7.90 m (8H, 2C6H4), 9.73 s (2H, 2CHO)
0.89 s (3H, Me), 1.25 s and 1.32 s (6H, Me2C), 1.30 3.00 m [5H, CH and (CH2)2], 3.86 s and 3.92 s (12H,
4COOMe), 7.05 8.10 m (20H, 2NH3, 2C6H4 and 2C6H3)
0.89 s (3H, Me), 1.25 s and 1.32 s (6H, Me2C), 1.20 3.00 m [5H, CH and (CH2)2], 6.25 br.s (6H, 2NH3), 6.65
8.05 m (14H, 2C10H7)
0.90 s (3H, Me), 1.25 s and 1.33 s (6H, Me2C), 1.40 3.05 m [5H, CH and (CH2)2], 6.50 br.s (6H, 2NH3), 6.85
8.00 m (14H, 2C10H7)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005

FUNCTIONALYZED NITROGEN- AND PHOSPHORUS-CONTAINING SALTS
Table 2. (Contd.)
63
Comp.
no.
, ppm
VIf
VIg
VIh
VIi
0.94 s (3H, Me), 1.24 s, 1.26 d, 1.32 s (12H, 2Me and Me2C), 1.05 3.30 m [31H, 7CH, 2CH2, (CH2)2 and
2(CH2)4], 6.08 br.s (4H, 2NH2)
0.94 s (3H, Me), 1.10 1.25 m (30H, 2Me, Me2C and 2Me3COO), 1.46 s and 1.54 s (12H, 2Me2CC C), 1.05
3.00 m [31H, 7CH, 2CH2, (CH2)2 and 2(CH2)4], 5.89 br.s (6H, 2OH and 2NH2)
0.90 s (3H, Me), 1.25 s and 1.33 s (6H, Me2C), 1.30 3.00 m [5H, CH and (CH2)2], 7.00 8.85 m (12H, 2C9H6N),
9.15 br.s (4H, 2OH and 2NH)
0.89 s (3H, Me), 1.25 s and 1.33 s (6H, Me2C), 1.35 3.00 m [5H, CH and (CH2)2], 7.05 7.85 m (30H, 6C6H5),
8.50 br.s (2H, 2PH)
VIIa
VIIb
1.40 6.00 m (10H, B10H10), 6.20 7.30 m (18H, 2OH, 2NH3 and 2C6H4)
1.40 6.10 m (10H, B10H10), 3.09 s (12H, 2Me2N), 6.65 7.80 m (8H, 2C6H4), 9.72 s (2H, 2CHO), 9.82 br.s (2H,
2NH)
VIIc
VIId
VIIe
VIIf
1.40 6.40 m (10H, B10H10), 3.92 s and 3.96 s (12H, 4COOMe), 7.10 8.20 m (20H, 2NH3, 2C6H4 and 2C6H3)
1.40 6.40 m (10H, B10H10), 6.50 8.15 m (20H, 2NH3 and 2C10H7)
1.40 6.40 m (10H, B10H10), 6.80 8.20 m (20H, 2NH3 and 2C10H7)
1.40 6.00 m (10H, B10H10), 0.80 3.30 m [26H, 6CH, 2CH2 and 2(CH2)4], 1.17 d (6H, 2Me), 7.15 br.s (4H,
2NH2)
VIIg
1.40 6.00 m (10H, B10H10), 0.70 3.70 m [28H, 2OH, 6CH, 2CH2 and 2(CH2)4], 1.17 br.s (24H, 2Me and
2Me3COO), 1.46 br.s (12H, 2Me2CC C), 7.20 br.s (4H, 2NH2)
VIIh
VIIi
1.40 6.00 m (10H, B10H10), 7.00 9.00 m (16H, 2OH, 2NH and 2C9H6N)
1.40 6.40 m (10H, B10H10), 6.80 7.90 m (30H, 6C6H5), 8.70 br.s (2H, 2PH)
Table 3. IR and UV spectra of Ia Ie, IIIa IIIt, IVa IVi, Va Vi, VIa VIi, and VIIa VIIi
Comp.
no.
UV spectrum,
max, nm ( )
1
IR spectrum, , cm
Ia
3700 2400 (OH); 3040 (=CH); 2975, 2957, 2934, 2872 (CHAlk); 1830, 1759, 1716 (C=O); 203 (3000)
1634 (C=C); 1468, 1445 (CH2); 1238, 1222, 1091, 950, 929 (C O)
2200 3600 (OH); 3080 (CHcarb); 2630, 2612, 2590, 2572, 2558 (BH); 1724 (C=O); 1428, 204 (200)
1280 (C O); 897 (CHcarb); 732, 712, 704 (BH)
Ib
Ic
2100 3650 (OH); 3066 (CHcarb); 2618 (BH); 1712 (C=O); 1421, 1289 (C O); 925 (CHcarb); 204(200), 220(150)
734, 719 (BH)
Id
3650 2300 (OH); 2980, 2974, 2890 (CHAlk); 1710, 1698 (C=O); 1475, 1459 (CH2); 1281, 215 (200)
1246, 1168, 1125 (C O)
Ie
3750 2200 (OH); 2670, 2626, 2695, 2585, 2531 (BH); 1720 (C=O); 1440, 1417, 1275 203 (150), 220 (50)
(C O); 915, 843, 723 (BH)
IIIa
IIIb
IIIc
IIId
IIIe
3045 (=CH); 2985, 2935, 2869 (CHAlk); 1824, 1779, 1704 (C=O); 1640 (C=C); 1466 (CH2); 204 (6000)
1231, 1087, 947, 923 (C O)
3045 (=CH); 2955, 2934, 2867 (CHAlk); 1860, 1840, 1781, 1710 (C=O); 1635 (C=C); 1468 204 (6000)
(CH2); 1232, 1080, 1040, 947, 924 (C O)
3040 (=CH); 2957, 2937, 2869 (CHAlk); 1842, 1780, 1707 (C=O); 1640 (C=C); 1467 (CH2); 204 (6000)
1231, 1086, 947, 923 (C O)
3386 (NH); 3040 (=CH); 2933, 2861 (CHAlk); 1857, 1843, 1782, 1696 (C=O); 1635 (C=C); 207 (6000)
1466, 1451 (CH2); 1231, 1086, 947, 923 (C O)
3382 (NH); 3075, 3040, 3010 (=CH and CHAr); 2956, 2933, 2869 (CHAlk); 1843, 1779, 207 (12000), 238
1693 (C=O); 1630 (C=C); 1602, 1499 (Ar); 1467, 1443 (CH2); 1277, 1231, 1086, 947, 923 (7000), 288 (1000)
(C O); 794, 752, 692 (CHAr)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005

64
DIKUSAR et al.
Table 3. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1
IR spectrum, , cm
IIIf
IIIg
IIIh
IIIi
IIIj
IIIk
3090, 3063, 3031 (=CH and CHAr); 2956, 2931, 2867 (CHAlk); 1855, 1842, 1779, 1696 210 (21000)
(C=O); 1637 (C=C); 1605, 1497 (Ar); 1456 (CH2); 1230, 1208, 1084, 947, 923 (C O); 751,
698 (CHAr)
3377 (NH); 3080, 3040, 3015 (=CH and CHAr); 2956, 2931, 2868 (CHAlk); 1855, 1824, 208 (19000),
1779, 1693 (C=O); 1630 (C=C); 1613, 1594, 1541, 1492 (Ar); 1466, 1447 (CH2); 1230, 242 (8000)
1086, 947, 923 (C O); 776, 757, 691 (CHAr)
3381 (NH); 3060, 3040, 3005 (=CH and CHAr); 2956, 2932, 2868 (CHAlk); 1842, 1778, 207 (23000),
1692 (C=O); 1625 (C=C); 1594, 1524, 1489 (Ar); 1466, 1446 (CH2); 1280, 1231, 1085, 248 (13000)
947, 923 (C O); 821, 756, 674 (CHAr)
3375 (NH); 3303 (OH); 3065, 3040, 3025 (=CH and CHAr); 2957, 2937, 2870 (CHAlk); 207 (19000),
1855, 1843, 1779, 1693 (C=O); 1640 (C=C); 1599, 1512, 1500 (Ar); 1461 (CH2); 1280, 235 (6000),
1228, 1085, 948, 924 (C O); 755 (CHAr)
285 (3000)
3065, 3040, 3025 (=CH and CHAr); 2960, 2932, 2868, 2825, 2739 (CHAlk); 1855, 1842, 204 (11000),
1779, 1716, 1691, 1660 (C=O); 1640 (C=C); 1596, 1552, 1534, 1373 (Ar); 1465, 1440 240 (4000),
(CH2); 1230, 1166, 1084, 1001, 946, 921, 905 (C O); 815, 753, 728, 693, 670, 595 (CHAr) 350 (13000)
3065, 3040, 3025 (=CH and CHAr); 2975, 2957, 2933, 2869, 2816, 2795, 2752 (CHAlk); 205 (12000),
1856, 1845, 1779, 1704 (C=O); 1637 (C=C); 1586, 1546, 1528, 1351 (Ar); 1458, 1444 239 (4000),
(CH2); 1230, 1192, 1176, 1160, 1088, 1076, 1002, 943, 919, 899 (C O); 828, 709, 669, 597 350 (14000)
(CHAr)
IIIl
3459, 3366 (NH); 3095, 3060, 3005 (=CH and CHAr); 2953, 2930, 2870 (CHAlk); 1855, 204 (22000),
1843, 1779, 1712 (C=O); 1623 (C=C); 1605, 1573, 1436, 1400, 1300 (Ar); 1465 (CH2); 242 (14000),
1277, 1255,1247, 1189, 1114, 1103, 1087, 1001, 947, 923, 906 (C O); 761, 704 (CHAr) 270 (8000)
3378 (NH); 3053, 3030, 3005 (=CH and CHAr); 2956, 2933, 2868 (CHAlk); 1855, 1842, 204 (45000),
1778, 1692 (C=O); 1632 (C=C); 1603, 1585, 1544, 1514, 1388 (Ar); 1470, 1447 (CH2); 238 (47000),
IIIm
1278, 1226, 1085, 947, 923, 905 (C O); 853, 813, 748, 671 (CHAr)
275 (7000)
IIIn
IIIo
IIIp
IIIq
3035 (=CH); 2939, 2865 (CHAlk); 1860, 1842, 1781, 1707 (C=O); 1630 (C=C); 1470, 1456, 205 (6000)
1445 (CH2); 1230, 1190, 1086, 1033, 1003, 947, 923, 905 (C O)
3035 (=CH); 2956, 2939, 2868 (CHAlk); 1860, 1843, 1780, 1696 (C=O); 1624 (C=C); 1460 206 (6000)
(CH2); 1232, 1192, 1105, 1087, 1024, 947, 923, 905 (C O)
3035 (=CH); 2960, 2936, 2865 (CHAlk); 1860, 1842, 1779, 1716 (C=O); 1621 (C=C); 1466, 205 (7000)
1449 (CH2); 1231, 1087, 1003, 947, 923, 905 (C O)
3080, 3055, 3040 (=CH and CHAr); 2958, 2935, 2870 (CHAlk); 1855, 1842, 1779, 1693 203 (8000),
(C=O); 1640 (C=C); 1596, 1387 (Ar); 1466, 1445 (CH2); 1231, 1087, 1004, 947, 923, 906 251 (2000), 259
(C O); 853, 752, 704 (CHAr)
(2000), 262 (2000)
IIIr
IIIs
IIIt
3405 (OH); 3075, 3053, 3040 (=CH and CHAr); 2957, 2934, 2869 (CHAlk); 1855, 1842, 203 (31000),
1779, 1691 (C=O); 1637 (C=C); 1580, 1505, 1472, 1406, 1380 (Ar); 1464, 1446 (CH2); 242 (34000)
1279, 1226, 1208, 1193, 1163, 1088, 947, 923, 905 (C O); 853, 825, 790, 709, 672 (CHAr)
3095, 3070, 3035 (=CH and CHAr); 2958, 2934, 2869 (CHAlk); 1855, 1845, 1779, 1692 205 (19000),
(C=O); 1623 (C=C); 1597, 1387 (Ar); 1227, 1210, 1086, 1005, 947, 923, 905 (C O); 853, 255 (6000),
747, 672 (CHAr)
275 (4000)
3070, 3053, 3030, 3000 (=CH and CHAr); 2955, 2928, 2867 (CHAlk); 1855, 1841, 1778, 205 (57000),
1690 (C=O); 1640 (C=C); 1585, 1433, 1386 (Ar); 1476, 1460 (CH2); 1278, 1228, 1085, 262 (7000)
1027, 1001, 946, 921, 904 (C O); 852, 742, 694, 671, 566, 540 (CHAr)
IVa
IVb
IVc
3077 (CHcarb); 2990, 2947, 2883 (CHAlk); 2614, 2595, 2574, 2557 (BH); 1672 (C=O); 1326, 206 (200), 250 (40)
1312 (C O); 841, 835 (CHcarb); 767, 718 (BH)
3204 (OH); 3077 (CHcarb); 2611, 2582 (BH); 1627 (C=O); 1615, 1570, 1493, 1470 (Ar); 208 (20000), 237
1358, 1273 (C O); 852 (CHcarb); 770, 719 (BH); 745 (CHAr)
(6000), 280 (3000)
3067 (CHcarb); 3004 (CHAr); 2955, 2918, 2862, 2825, 2810 (CHAlk); 2625, 2605, 2580 204 (10000), 245
(BH); 1736, 1614 (C=O); 1538, 1484, 1440 (Ar); 1382, 1260, 1174 (C O); 811, 730, 716, (6000), 340 (25000)
636, 610 (CHAr and BH)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005

FUNCTIONALYZED NITROGEN- AND PHOSPHORUS-CONTAINING SALTS
Table 3. (Contd.)
65
Comp.
no.
UV spectrum,
max, nm ( )
1
IR spectrum, , cm
IVd
IVe
IVf
3076 (CHcarb); 2960, 2930, 2861 (CHAlk); 2619, 2605, 2592, 2560, 2550, 2525, 2428 (BH); 206 (150), 212(100)
1668, 1648 (C=O); 1455, 1447 (CH2); 1338 (C O); 843 (CHcarb); 772, 718 (BH)
3072 (CHcarb); 2990, 2975, 2960, 2947, 2940, 2864, 2830 (CHAlk); 2625, 2607, 2576, 2560 208(500), 221(300),
2551, 2496 (BH); 1721, 1666, 1598 (C=O); 1353 (C O); 843 (CHcarb); 767, 721 (BH) 313 (50)
3140, 3105, 3075, 3025 (CHAr); 3060 (CHcarb); 2622, 2570, 2555, 2543 (BH); 1655, 1636 204 (2500), 240
(C=O); 1608, 1550, 1490 (Ar); 1331, 1251 (C O); 845 (CHcarb); 770, 756, 718, 687, 589 (800), 244 (1000),
(CHAr and BH)
252 (1400), 256
(1500), 263 (900)
IVg
3125, 3100, 3045 (CHAr); 3070 (CHcarb); 2648, 2608, 2568, 2541 (BH); 1652, 1640 (C=O); 205 (30000), 242
1596, 1555, 1474, 1409 (Ar); 1327, 1304, 1275 (C O); 845 (CHcarb); 814, 805, 771, 745, (40000), 310 (2000)
714, 621, 580, 543 (CHAr and BH)
IVh
IVi
3100, 3080, 3030 (CHAr); 3071 (CHcarb); 2605, 2580 (BH); 1727 (C=O); 1623, 1597 (Ar); 205 (14000), 255
1396, 1349, 1282, 1215 (C O); 838 (CHcarb); 770, 748, 730, 714 (CHAr and BH) (3500), 270 (2500)
3100, 3080, 3045, 3026, 3010, 3000 (CHAr); 3074 (CHcarb); 2607, 2570 (BH); 1733, 1655 205 (33000), 265
(C=O); 1583, 1475, 1440 (Ar); 1261, 1120 (C O); 840 (CHcarb); 742, 730, 710, 691, 491 (8000)
(CHAr and BH)
Va
Vb
Vc
3060 (CHcarb); 3014, 2987, 2946, 2882 (CHAlk); 2654, 2645, 2625, 2593 (BH); 1631 (C=O); 207 (200), 220(100)
1443 (CH2); 1331 (C O); 833 (CHcarb); 783, 771, 749, 730 (BH)
3246 (OH); 3080, 3050, 3030 (CHAr); 3061 (CHcarb); 2604 (BH); 1623 (C=O); 1610, 1575, 208 (21000), 238
1499, 1469 (Ar); 1361, 1280, 1120 (C O); 853 (CHcarb); 739, 725 (CHAr and BH) (5000), 280 (3000)
3060, 3010 (CHAr); 3031 (CHcarb); 2950, 2918, 2850, 2831, 2810, 2781 (CHAlk); 2603, 205 (10000), 245
2573 (BH); 1733, 1591 (C=O); 1536, 1484, 1441 (Ar); 1380, 1274, 1251, 1171, 1125 (7000), 340 (24000)
(C O); 840 (CHcarb); 812, 730, 714, 635, 600 (CHAr and BH)
Vd
Ve
Vf
3050 (CHcarb); 3025, 2960, 2932, 2863, 2743 (CHAlk); 2650, 2593 (BH); 1653, 1640, 1620 207 (150), 211(100)
(C=O); 1472, 1454, 1440, 1435 (CH2); 1349, 1330, 1322, 1119 (C O); 867 (CHcarb); 784,
768, 749, 728, 624, 559 (BH)
3060 (CHcarb); 2983, 2942, 2864, 2830, 2775, 2740 (CHAlk); 2603 (BH); 1726, 1650 (C=O;) 207 (500), 220
1460, 1450 (CH2); 1350, 1131, 1117 (C O); 855 (CHcarb); 780, 766, 750, 727, 624, 609, (300), 312 (50)
577 (BH)
3205, 3145, 3134, 3102, 3073 (CHAr); 3060 (CHcarb); 2661, 1612, 2581 (BH); 1690 (C=O); 205 (3000), 240
1605, 1533, 1485 (Ar); 1340, 1311, 1270, 1251, 1199, 1169, 1050 (C O); 840 (CHcarb); (800), 245 (1000),
782, 770, 749, 730, 715, 675 (CHAr and BH)
253 (1500), 255
(2000), 264 (1000)
Vg
Vh
3102, 3030 (CHAr); 3060 (CHcarb); 2601 (BH); 1647 (C=O); 1617, 1591, 1546, 1471, 1407, 204 (30000), 243
1382 (Ar); 1348, 1325, 1299, 1269, 1199, 1115, 1103 (C O); 860 (CHcarb); 822, 805, 770, (41000), 311 (2000)
748, 724, 710, 623, 580 (CHAr and BH)
3110, 3048, 3000 (CHAr); 3060 (CHcarb); 2645, 2610, 2598, 2580 (BH); 1717 (C=O); 1625, 205 (15000), 255
1600, 1458 (Ar); 1290, 1272, 1213, 1136, 1046 (C O); 845 (CHcarb); 779, 760, 744, 722, (4000), 272 (3000)
655, 621 (CHAr and BH)
Vi
3095, 3050, 3020, 3010, 3000 (CHAr); 3058 (CHcarb); 2655, 2609 (BH); 1711, 1647 (C=O); 205 (34000), 265
1582, 1475, 1434, 1430, 1420 (Ar); 1285, 1228, 1121, 1089, 1067 (C O); 855 (CHcarb); (7000)
755, 741, 718, 692, 619, 539, 512, 490 (CHAr and BH)
VIa
VIb
3375, 3304 (OH and NH); 3100, 3051, 3025 (CHAr); 2980, 2974, 2894, 2850 (CHAlk); 208 (37000), 235
1710, 1697 (C=O); 1605, 1512, 1471, 1405, 1377 (Ar); 1282, 1269, 1218, 1169, 1125, (10000), 290 (5000)
1086 (C O); 924, 898, 847, 804, 765, 742 (CHAr)
3090, 3055, 3025 (CHAr); 2990, 2973, 2950, 2901, 2823, 2796 (CHAlk); 1710, 1693, 1682, 204 (18000), 242
1661 (C=O); 1600, 1549, 1535 (Ar); 1459 (CH2); 1374, 1314, 1281, 1247, 1233, 1166, (12000), 340
1125 (C O); 938, 825, 813, 728, 596 (CHAr)
(52000)
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66
DIKUSAR et al.
Table 3. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1
IR spectrum, , cm
VIc
VId
VIe
3459, 3367 (NH); 3095, 3060, 3040 (CHAr); 3000, 2985, 2975, 2953, 2890, 2840 (CHAlk); 203 (44000), 245
1712 (C=O); 1624, 1606, 1574, 1560, 1455, 1437, 1401 (Ar); 1300, 1277, 1255, 1250, (45000), 280
1115, 1000 (C O); 910, 868, 828, 761, 705 (CHAr)
(23000), 345 (5000)
3411, 3343, 3225 (NH); 3085, 3055, 3043 (CHAr); 2985, 2973, 2920, 2880 (CHAlk); 1710, 212 (85000), 243
1696, 1635 (C=O); 1624, 1590, 1575, 1513, 1459, 1406, 1376 (Ar); 1288, 1247, 1167, (46000), 370
1125, 1013 (C O); 792, 770, 717 (CHAr)
(10000)
3394, 3317, 3201 (NH); 3085, 3048, 3025, 3000 (CHAr); 2990, 2974, 2950, 2890 (CHAlk); 212 (34000), 240
1710, 1697, 1630 (C=O); 1599, 1512, 1470, 1376 (Ar); 1281, 1225, 1223, 1183, 1124 (82000), 270 (6000),
(C O); 855, 845, 814, 742, 713 (CHAr)
280 (7000), 290
(6000)
VIf
VIg
VIh
2975, 2939, 2863 (CHAlk); 1720, 1623 (C=O); 1458 (CH2); 1383, 1357, 1304, 1243, 1132 205 (1500), 220
(C O) (1500)
2982, 2937, 2863 (CHAlk); 1623 (C=O); 1458 (CH2); 1386, 1362, 1244, 1200, 1157 (C O); 204 (1000)
872 (O O)
3090, 3065, 3048, 3030 (CHAr); 2990, 2974, 2891 (CHAlk); 1709, 1697 (C=O); 1579, 1508, 205 (18000), 242
1473, 1434, 1410, 1379 (Ar); 1285, 1275, 1246, 1223, 1207, 1167, 1125, 1093, 1059 (C O); (25000), 325 (3000)
818, 781, 742, 711, 637 (CHAr)
VIi
3080, 3066, 3050, 3025, 3015, 3000 (CHAr); 2970, 2885 (CHAlk); 1710, 1697 (C=O); 1583, 210 (68000), 260
1475, 1434, 1376 (Ar); 1280, 1246, 1168, 1121, 1090, 1025 (C O); 742, 723, 696, 542, (26000)
513, 499, 492 (CHAr)
VIIa
VIIb
VIIc
VIId
VIIe
3375, 3304 (OH and NH); 3090, 3055, 3025 (CHAr); 2650, 2618, 2595, 2560 (BH); 1624 208 (40000), 235
(C=O); 1605, 1570, 1507, 1492, 1470, 1407 (Ar); 1346, 1321, 1277, 1190, 1132 (C O); (11000), 290 (6000)
897, 853, 741, 550 (BH and CHAr)
3095, 3050, 3000 (CHAr); 2950, 2918, 2855, 2828 (CHAlk); 2637, 2600, 2571 (BH); 1726, 205 (19000),
1660 (C=O); 1598, 1536, 1440 (Ar); 1379, 1320, 1260, 1232, 1170, 1065 (C O); 817, 730, 245 (13000),
634, 606, 506 (BH and CHAr)
341 (55000)
3459, 3366 (NH); 3095, 3060, 3040, 3000 (CHAr); 2951, 2900, 2845 (CHAlk); 2610 (BH); 203 (43000),
1713 (C=O); 1623, 1606, 1573, 1437, 1400 (Ar); 1300, 1277, 1260, 1250, 1196, 1115, 245 (44000), 280
1000 (C O); 870, 761, 730, 705 (BH and CHAr)
(24000), 350 (6000)
3412, 3344 (NH); 3055, 3045 (CHAr); 2670, 2602, 2560 (BH); 1719, 1625 (C=O); 1603, 212 (84000), 244
1577, 1545, 1515, 1455, 1404 (Ar); 1349, 1273, 1130 (C O); 794, 768, 730, 703 (BH and (47000), 370 (9000)
CHAr)
3395, 3319, 3200 (NH); 3050, 3005 (CHAr); 2670, 2626, 2611, 2585 (BH); 1740, 1626 212 (35000), 240
(C=O); 1608, 1564, 1513, 1469, 1372 (Ar); 1281, 1269, 1225, 1184, 1137, 1124 (C O); (83000), 270 (5000),
848, 810, 773, 743, 705, 624, 470 (BH and CHAr)
280 (6000), 290
(5000)
VIIf
VIIg
VIIh
2975, 2940, 2862 (CHAlk); 2605 (BH); 1723, 1650 (C=O); 1450 (CH2); 1340, 1130 (C O); 205 (1500),
770, 754, 739, 608, 576, 501 (BH) 315 (100)
2983, 2938, 2862 (CHAlk); 2607 (BH); 1646 (C=O); 1454 (CH2); 1362, 1336, 1244, 1190, 205 (1500)
1157, 1127, 1071, 1037 (C O); 871 (O O); 754, 737, 586, 524 (BH)
3419 (OH); 3090, 3068, 3025 (CHAr); 2608 (BH); 1733, 1713, 1634 (C=O); 1603, 1595, 205 (19000), 242
1557, 1504, 1473, 1420, 1400, 1375 (Ar); 1334, 1307, 1274, 1208, 1099 (C O); 821, 803, (26000), 330 (3000)
780, 765, 751, 725, 710, 622, 576 (CHAr)
VIIi
3085, 3067, 3047, 3030, 3010, 3000 (CHAr); 2611 (BH); 1739, 1634 (C=O); 1583, 1475, 211 (70000),
1435 (Ar); 1237, 120, 1089, 1069, 1025, 997 (C O); 742, 723, 695, 619, 541, 513, 498, 262 (27000)
490 (CHAr)
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FUNCTIONALYZED NITROGEN- AND PHOSPHORUS-CONTAINING SALTS
67
Ie, IVb, IVe, IVg, Vb, Vg,VIa VIi, and VIIa VIIi),
10. Gonis, G., Slezak, F.B., and Lawson, N.E., Ind. Eng.
Chem. Prod. Res. Develop., 1973, vol. 12, no. 4,
p. 326.
reference TMS. The UV spectra were obtained on a
3
Specord UV-Vis spectrophotometer for 1 10
M
solutions in n-butanol. Thermal analysis was per-
formed on a Paulic Paulic Erdey derivatograph in
argon, linear heating rate 7 deg/min, sample 100 mg,
DTA 1/10, and DTG 1/10 [35]. Maleopimaric acid
was prepared and purified as described in [10], o- and
m-carborane-1-carboxylic acids and m-carborane-1,7-
dicarboxylic acid were prepared as described in [36].
11. Ayer, A., McDonald, C.E., and Stothers, J.B., Can.
J. Chem., 1963, vol. 41, no. 5, p. 1113.
12. Scebacher, W., Hufner, A., Haslinger, E., and Weis, R.,
Monatsh. Chem., 1998, vol. 129, nos. 6 7, p. 697.
13. Tolstikov, G.A., Tolstikova, O.B., Khlebnikova, T.B.,
Zakharova, I.V., and Zamaraev, K.I., Abstracts of
Papers, 2 Soveshchanie Lesokhimiya i organicheskii
sintez (2nd Conf. Wood Chemistry and Organic
Synthesis ), 1996, p. 45.
Nitrogen- and phosphorus-containing carboxylic
acid salts IIIa IIIt, IVa IVi, Va Vi, VIa VIi, and
VIIa VIIi (general procedure). Compound II,
0.05 mol, was added to a solution of 0.005 mol of
acid Ia Ic in 20 ml of absolute chloroform (or
0.0025 mol of acid Id or If in 20 ml of absolute
methanol). When compound II had dissolved com-
pletely, the solvent was removed, and the residue
subjected to a vacuum at a temperature not higher
than 40 50 C. Salts IIIa IIIt, IVa IVi, Va Vi, VIa
VIi, and VIIa VIIi were obtained as homogeneous
brittle porous materials.
14. Panda, P. and Panda, H., Pesticides, 1988, vol. 22,
no. 1, p. 38.
15. JP Patent Application 57-88102, 1982, Ref. Zh. Khim.,
1983, 22O277P.
16. GB Patent 1400481, 1975, Ref. Zh. Khim., 1976,
8O130P.
17. Schuller, W.H. and Lawrence, R.V., J. Chem. Eng.
Data, 1967, vol. 12, no. 2, p. 267.
18. Penczek, P., Roczn. Chem., 1970, vol. 44, no. 9,
p. 1815.
ACKNOWLEDGMENTS
19. Lewis, J.B., Lloyd, W.D., and Hedrick, G.W., J. Org.
Chem., 1960, vol. 25, no. 7, p. 1206.
The work was financially supported by INTAS
(grant no. 9-00806) and INTERBIO-SCREEN Co.
(Moscow).
20. Fieser, L. and Fieser, M., Steroids, New York: Rein-
hold, 1959. Translated under the title Steroidy,
Moscow: Mir, 1964, p. 19.
21. Locher, G.L., Am. J. Roentgenol. Radium Ther., 1936,
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