Page 5 of 7
The Journal of Organic Chemistry
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mmol benzylalchohol derivative was added to the anodic
142.9, 155.8, 156.5, 161.4. Anal. Calcd for C14
69.12; H, 5.39; N, 5.76. Found: C, 69.25; H, 5.72; N, 5.61.
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3
H13NO : C,
compartment. Three graphite rods were placed in each
compartment. The cathodic solution was degassed by Argon
flow and solution was electrolyzed under a constant-current
(Z)-1-phenyl-N-(p-tolyl)methanimine oxide (3f):
2
o
1
density of 0.3 mA/cm . The electrolysis progress was checked
Isolated yield: 75% (0158 g). m.p =106-108 C. H NMR, δ ppm
(300 MHz, DMSO-d ): 2.36 (s, 3H), 7.33 (d, J = 8.3 Hz, 2H),
7.48 (m, 3H), 7.79 (d, J = 8.4 Hz, 2H), 8.46 (m, 3H). C NMR
by cyclic voltammetry and was stopped when the decay of the
6
퐶0
13
nitrobenzen (퐼푝 ) cathodic peak current became about 90% of
1
its initial value. At the end of electrolysis, anodic and cathodic
solutions were mixed, its pH was adjusted to 3.0 by addition of
NaOH solution and allowed to react overnight under stirring.
After evaporation of ethanol, the precipitated products were
collected by filtration, washed with distilled water (several
{ H}, δ ppm (75 MHz, DMSO-d
129.4, 130.4, 131.2, 132.8, 139.6, 146.2. Anal. Calcd for
13NO: C, 79.59; H, 6.20; N, 6.63. Found: C, 79.41; H, 6.51;
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): 20.6, 121.2, 128.4, 128.7,
14
C H
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N, 6.49.
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(Z)-1-(4-chlorophenyl)-N-(p-tolyl)methanimine oxide (3g):
times) and after drying were purified by
a column
o
1
chromatography with n-hexane/EtOAc (5:1 to 2:1) to afford the
Isolated yield: 78% (0.191 g). m.p =105-108 C. H NMR, δ
ppm (300 MHz, DMSO-d ): 2.31 (s, 3H), 7.17-7.23 (m, 4H),
7.57 (d, J = 8.5 Hz, 2H), 7.92 (d, J = 8.5 Hz, 2H), 8.63 (s, 1H).
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13
corresponding nitrones and analyzed by HNMR, CNMR and
CHN.
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1
3
1
C NMR { H}, δ ppm (75 MHz, DMSO-d
29.6, 130.0, 134.9, 135.6, 135.7, 148.3, 158.3. Anal. Calcd for
12ClNO: C, 68.44; H, 4.92; N, 5.70. Found: C, 68.55; H,
.04; N, 5.68.
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): 21.1, 120.9, 128.8,
1
CHARACTERISTICS OF SYNTHESIZED NITRONES 3A-3J:
14
C H
5
(Z)-N,1-diphenylmethanimine oxide (3a):
o
1
Isolated yield: 74% (0.145 g). m.p =113-115 C. H NMR, δ
ppm (300 MHz, acetone d ): 7.47-7.53 (m, 6H), 7.90-7.93 (m,
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(
Z)-N-(4-chlorophenyl)-1-phenylmethanimine oxide (3h):
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2
H), 8.34 (s, 1H), 8.51-8.54 (m, 2H). 13C NMR { H}, δ ppm (75
o
1
Isolated yield: 67% (160 g). m.p =105-108 C. H NMR, δ ppm
300 MHz, DMSO-d ): 7.49 (t, J = 3.5 Hz, 3H), 7.61 (d, J = 8.8
Hz, 2H), 7.92 (d, J = 8.8 Hz, 2H), 8.44-8.48 (m, 2H), 8.53 (s,
MHz, acetone d
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): 122.3, 129.1, 129.5, 129.8, 130.5, 131.1,
11NO: C, 79.17; H,
.62; N, 7.10. Found: C, 78.98; H, 5.91; N, 7.11.
(
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1
5
32.5, 133.7, 150.1. Anal. Calcd for C13H
1
3
1
1). C NMR { H}, δ ppm (75 MHz, DMSO-d
128.9, 129.0, 130.9, 130.9, 133.8, 134.2, 147.1. Anal. Calcd for
10ClNO: C, 67.40; H, 4.35; N, 6.05. Found: C, 67.65; H,
.62; N, 5.94.
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): 123.3, 128.5,
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(
Z)-1-(4-chlorophenyl)-N-phenylmethanimine oxide (3b):
13
C H
4
o
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Isolated yield: 78% (0.180 g). m.p =154-156 C. H NMR, δ
ppm (300 MHz, acetone d ): 7.49-7.55 (m, 5H), 7.89-7.93 (m,
H), 8.40 (s, 1H), 8.54 (d, J = 7.5 Hz, 2H). 13C NMR { H}, δ
ppm (75 MHz, acetone d ): 122.3, 129.3, 129.8, 130.7, 131.0,
131.2, 132.7, 135.7, 150.0. Anal. Calcd for C13 10ClNO: C,
7.40; H, 4.35; N, 6.05. Found: C, 67.28; H, 4.51; N, 5.98.
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(
Z)-N,1-bis(4-chlorophenyl)methanimine oxide (3i):
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o
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Isolated yield: 70% (0.186 g). m.p =194-196 C. H NMR, δ
ppm (300 MHz, DMSO-d ): 7.30 (d, J = 8.4 Hz, 3H), 7.46 (d, J
8.4Hz, 2H), 7.69 (d, J = 8.8 Hz, 2H), 8.26 (d, J = 8.8, 2H),
H
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=
8
1
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13
1
.64 (s, 1). C NMR { H}, δ ppm (75 MHz, DMSO-d
26.8, 129.1, 129.3, 130.3, 133.8, 134.6, 141.9, 160.2. Anal.
Cl NO: C, 58.67.40; H, 3.41; N, 5.26. Found:
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): 123.9,
(
Z)-N-(4-hydroxyphenyl)-1-phenylmethanimine oxide (3c):
o
1
Isolated yield: 70% (0.149 g). m.p =120-122 C. H NMR, δ
ppm (300 MHz, acetone d ): 6.78 (d, J = 7.5 Hz, 2H), 7.18 (d, J
7.5 Hz, 2H), 7.48 (t, J = 7.6, 3H), 7.86-7.89 (m, 2H). C NMR
Calcd for C13
H
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2
6
C, 58.78; H, 3.62; N, 5.67.
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=
{
1
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H}, δ ppm (75 MHz, acetone d ): 115.7, 122.53, 128.2, 128.7,
(
Z)-N-(4-chlorophenyl)-1-(4-methoxyphenyl)methanimine
oxide (3j):
Isolated yield: 67% (0.175). m.p =135-137 C. H NMR, δ ppm
300 MHz, DMSO-d ): 3.82 (s, 3H), 7.06 (d, J = 8.8 Hz, 2H),
.59 (d, J = 8.9 Hz, 2H), 7.94 (d, J = 8.9 Hz, 2H), 8.46 (d, 3.6,
30.8, 136.4, 142.5, 156.2, 157.2. Anal. Calcd for C13
H
2
11NO :
C, 73.23; H, 5.20; N, 6.57. Found: C, 73.10; H, 5.51; N, 6.49.
o
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(Z)-1-(4-chlorophenyl)-N-(4-hydroxyphenyl)methanimine
oxide (3d):
(
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H). C NMR { H}, δ ppm (75 MHz, DMSO-d
23.1, 123.8, 128.9, 131.0, 133.8, 142.4, 146.9, 160.9. Anal.
: C, 64.25; H, 4.62; N, 5.35. Found: C,
64.10; H, 4.91; N, 5.24.
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): 55.3, 113.9,
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Isolated yield: 73% (0.18 g). m.p =178-179 C. H NMR, δ ppm
300 MHz, DMSO-d ): 6.78 (d, J = 8.7 Hz, 2H), 7.20 (d, J = 8.7
Hz, 2H), 7.54 (d, J = 8.4, 2H), 7.89 (d, J = 8.4, 2H). C NMR
(
6
Calcd for C14H12ClNO
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{
H}, δ ppm (75 MHz, DMSO-d
35.2, 135.3, 142.1, 155.7, 156.4. Anal. Calcd for
: C, 63.04; H, 4.07; N, 5.66. Found: C, 62.91; H,
.18; N, 5.55.
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): 115.6, 122.5, 128.8, 129.7,
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(Z)-1-(3-nitrophenyl)-N-phenylmethanimine oxide (3k):
13 2
C H10ClNO
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Isolated yield: 72% (0.162 g). m.p = 149-151 C. H NMR, δ
ppm (300 MHz, DMSO-d ): 6.78 (m,3H), 7.20 (t, J = 8.1 Hz,
H), 7.54 (m, 2H), 7.89 (d, J = 6.9, 1H), 8.64 (s, 3H), 7.89 (d, J
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-
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=
(Z)-N-(4-hydroxyphenyl)-1-(4-methoxyphenyl)methanimine
oxide (3e):
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1
8.7, 1H), 9.61 (s, 1H). C NMR { H}, δ ppm (75 MHz,
): 122.4, 123.3, 125.2, 129.9, 130.5, 131.1, 132.2,
33.8, 135.2, 149.2, 149.8. Anal. Calcd for C13 : C,
4.46; H, 4.16; N, 11.56. Found: C, 64.71; H, 4.18; N, 11.48.
acetone-d
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o
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Isolated yield: 73% (0.153 g). m.p =173-175 C. H NMR, δ
ppm (300 MHz, DMSO-d ): 3.81 (s, 3H), 6.76 (d, J = 8.4 Hz,
H), 7.02 (d, J = 8.2 Hz, 2H), 7.13 (d, J = 8.4, 2H), 7.82 (d, J =
10 2 3
H N O
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.2, 2H), 8.50 (s, 1H), 9.41 (s, 1H). C NMR { H}, δ ppm (75
): 55.3, 114.1, 115.6, 122.2, 129.3, 129.9,
(
Z)-1-(3-nitrophenyl)-N-(p-tolyl)methanimine oxide (3l):
MHz, DMSO-d
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o
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Isolated yield: 70% (0.172 g). m.p =131-132 C. H NMR, δ
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