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022
D. Bhuniya et al.
PAPER
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.9 Hz, 1 H), 8.13 (s, 1 H), 8.60 (dd, J = 4.9, 1.9 Hz, 1 H), 8.72 (d,
LC-MS (CI): m/z = 269 (M + 1, 100%).
J = 1.9 Hz, 1 H).
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3
Phenyl 2-(4-Methanesulfonyloxybenzylideneaminoxy)ethyl
Sulfone (3er)
Mp 89–90 °C.
C NMR (CDCl , 50 MHz): δ = 18.02, 68.24, 117.25, 123.41,
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27.38, 133.40, 147.05, 148.36, 150.64.
LC-MS (CI): m/z = 176 (M + 1, 100%).
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IR (neat): 2939, 1500, 1365, 1154 cm .
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Phenyl 2-(Pyridin-3-ylmethylideneaminoxy)ethyl Sulfone (3cr)
H NMR (CDCl , 500 MHz): δ = 3.16 (s, 3 H), 3.57 (t, J = 5.8 Hz,
3
Purity (HPLC) 96%.
2 H), 4.52 (t, J = 5.8 Hz, 2 H), 7.27 (d, J = 8.8 Hz, 2 H), 7.49–7.55
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(aromatic, 4 H), 7.62 (t, J = 7.3 Hz, 1 H), 7.66 (s, 1 H), 7.93 (d,
J = 8.8 Hz, 2 H).
IR (neat): 2927, 1316, 1146 cm .
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H NMR (CDCl , 400 MHz): δ = 3.57 (t, J = 6.1 Hz, 2 H), 4.52 (t,
J = 6.1 Hz, 2 H), 7.26 (dd, J = 8.2, 4.9 Hz, 1 H), 7.51 (t, J = 7.8, Hz,
H), 7.57–7.62 (aromatics, 1 H), 7.64 (s, 1 H), 7.79 (dt, J = 7.8, 1.9
Hz, 1 H), 7.91 (d, J = 8.2 Hz, 2 H), 8.56 (d, J = 1.9 Hz, 1 H), 8.58
3
13
C NMR (CDCl , 125 MHz): δ = 37.54, 55.47, 67.27, 122.31 (2 C),
3
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28.05 (2 C), 128.56 (2 C), 129.04 (2 C), 130.70, 133.58, 139.75,
48.16, 150.07.
2
(
d, J = 1.9 Hz, 1 H).
LC-MS (CI): m/z = 384 (M + 1, 100%).
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3
C NMR (CDCl , 50 MHz): δ = 55.19, 67.17, 123.32, 127.26,
Anal. Calcd for C H NO S : C, 50.12; H, 4.47; N, 3.65. Found C,
3
16 17
6 2
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27.80 (2 C), 128.79 (2 C), 133.20, 133.34, 139.54, 146.54, 148.25,
50.60.
50.37; H, 4.79; N, 3.61.
Phenyl 2-(3-Methybutylideneaminoxy)ethyl Sulfone (3fr)
Purity (HPLC) 99.4%.
LC-MS (CI): m/z = 291 (M + 1, 100%).
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Ethyl 3-(Thiophen-3-ylmethylideneaminoxy)propanoate (3dp)
IR (neat): 2959, 1320, 1145 cm .
Purity (HPLC) 97%.
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H NMR (CDCl , 200 MHz): δ = 0.87 (d, J = 6.7 Hz, 6 H), 1.60–
3
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IR (neat): 3103, 2982, 1735, 1186, 1046 cm .
1.80 (m, 1 H), 1.92 (t, J = 6.6 Hz, 2 H), 3.50 (t, J = 6.1 Hz, 2 H),
4.35 (t, J = 6.1 Hz, 2 H), 6.99 (t, J = 6.6 Hz, 1 H), 7.50–7.70 (aro-
matic, 3 H), 7.92 (d, J = 7.2 Hz, 2 H).
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H NMR (CDCl , 400 MHz): δ = 1.26 (t, J = 7 Hz, 3 H), 2.72 (t,
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J = 6.3 Hz, 2 H), 4.17 (q, J = 7 Hz, 2 H), 4.41 (t, J = 6.3 Hz, 2 H),
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3
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.31 (dd, J = 5, 3 Hz, 1 H), 7.39 (dd, J = 5, 1 Hz, 1 H), 7.42 (dd,
C NMR (CDCl , 50 MHz): δ = 22.05, 26.27, 37.81, 55.43, 66.27,
3
J = 3, 1 Hz, 1 H), 8.10 (s, 1 H).
128.03 (2 C), 128.90 (2 C), 133.44, 139.78, 151.50.
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3
C NMR (CDCl , 50 MHz): δ = 14.08, 34.52, 60.44, 69.28, 124.75,
LC-MS (CI): m/z = 270 (M + 1, 100%).
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26.27, 126.50, 134.40, 144.25, 171.28.
Phenyl 2-(Cyclohexylmethylideneaminoxy)ethyl Sulfone (3gr)
LC-MS (CI): m/z = 228 (M + 1, 100%).
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Isolated as mixture of cis and trans (1:4 by HPLC and C NMR))
isomers. This is because the starting oxime itself was a mixture of
cis and trans isomers. NMR data are given for the trans isomer only
for simplicity.
2
-(Thiophen-3-ylmethylideneaminoxy)ethylcyanide (3dq)
Purity (HPLC) 98%.
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IR (neat): 3103, 2942, 2252, 1054 cm .
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1
IR (neat): 2929, 2855, 1449, 1320, 1146 cm .
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H NMR (CDCl , 400 MHz): δ = 2.77 (t, J = 6.4 Hz, 2 H), 4.33 (t,
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H NMR (CDCl , 200 MHz): δ = 1.00–1.32 (m, 6 H), 1.60–1.75 (m,
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J = 6.4 Hz, 2 H), 7.33 (dd, J = 5.2, 2.8 Hz, 1 H), 7.39 (dd, J = 5.2, 1
Hz, 1 H), 7.48 (dd, J = 2.8, 1 Hz, 1 H), 8.16 (s, 1 H).
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H), 2.00–2.10 (m, 1 H), 3.49 (t, J = 6.2 Hz, 2 H), 4.33 (t, J = 6.2
Hz, 2 H), 6.87 (d, J = 6.4 Hz, 1 H), 7.54 (t, J = 7.5 Hz, 2 H), 7.63 (t,
J = 7.5 Hz, 1 H), 7.92 (d, J = 7.5 Hz, 2 H).
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3
C NMR (CDCl , 50 MHz): δ = 18.18, 67.99, 117.50, 124.64,
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26.74, 127.09, 133.76, 145.43.
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3
C NMR (CDCl , 50 MHz): δ = 25.11, 25.55, 29.97, 38.16, 55.38,
3
LC-MS (CI): m/z = 181 (M + 1, 100%).
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6.26, 128.03 (2 C), 128.88 (2 C), 133.41, 139.84, 155.95.
LC-MS (CI): m/z = 296 (M + 1, 100%).
Phenyl 2-(Thiophen-3-ylmethylideneaminoxy)ethyl Sulfone
(
3dr)
Ethyl 3-(3-Phenylprop-2-enylideneaminoxy)propanoate (3hp)
Purity (HPLC) 98%.
Purity (HPLC) 98%.
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IR (neat): 3102, 2928, 1607, 1315, 1146 cm .
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1
IR (neat): 2983, 1736, 1187, 1037 cm .
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H NMR (CDCl , 400 MHz): δ = 3.57 (t, J = 6.1 Hz, 2 H), 4.47 (t,
3
1
H NMR (CDCl , 400 MHz): δ = 1.26 (t, J = 7 Hz, 3 H), 2.70 (t,
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J = 6.1 Hz, 2 H), 7.27–7.35 (aromatic, 3 H), 7.53 (t, J = 7.6 Hz, 2
H), 7.61 (d, J = 7.5 Hz, 1 H), 7.68 (s, 1 H), 7.93 (d, J = 7.5 Hz, 2 H).
J = 6.4 Hz, 2 H), 4.17 (q, J = 7 Hz, 2 H), 4.37 (t, J = 6.4 Hz, 2 H),
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.78–6.80 (m, 2 H), 7.26–7.36 (aromatic, 3 H), 7.41–7.44 (aromat-
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C NMR (CDCl , 50 MHz): δ = 55.21, 66.74, 124.35, 126.51,
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ic, 2 H), 7.86 (dd, J = 6.7, 1.6 Hz, 1 H).
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26.74, 127.78 (2 C), 128.79 (2 C), 133.33, 133.53, 139.53, 144.76.
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3
C NMR (CDCl , 50 MHz): δ = 14.16, 34.50, 60.55, 69.43, 121.79,
3
LC-MS (CI): m/z = 296 (M + 1, 100%).
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26.86 (2 C), 128.75 (2 C), 128.79, 135.91, 138.65, 150.98, 171.28.
LC-MS (CI): m/z = 248 (M + 1, 100%).
2
-(4-Methanesulfonyloxybenzylideneaminoxy)ethylcyanide
(
3eq)
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IR (neat): 2931, 2252, 1388, 1153 cm .
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2-(3-Phenylprop-2-enylideneaminoxy)ethylcyanide (3hq)
IR (neat): 2937, 2252, 1049 cm .
H NMR (CDCl , 500 MHz): δ = 2.78 (t, J = 6.2 Hz, 2 H), 3.16 (s,
H), 4.37 (t, J = 6.2 Hz, 2 H), 7.31 (d, J = 8.8 Hz, 2 H), 7.65 (d,
3
–1
3
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J = 8.8 Hz, 2 H), 8.12 (s, 1 H).
H NMR (CDCl , 400 MHz): δ = 2.75 (t, J = 6.5 Hz, 2 H), 4.29 (t,
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J = 6.5 Hz, 2 H), 6.75–6.87 (m, 2 H), 7.29–7.38 (aromatic, 3 H),
C NMR (CDCl , 125 MHz): δ = 18.32, 29.60, 37.56, 68.37,
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.45 (d, J = 7.6 Hz, 2 H), 7.93 (d, J = 8.6 Hz, 1 H).
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17.42, 122.40 (2 C), 128.77 (2 C), 130.81, 148.73, 150.22.
Synthesis 2003, No. 7, 1018–1024 ISSN 0039-7881 © Thieme Stuttgart · New York