Molecules 2013, 18
7369
1
2
-(4-Nitrophenyl)-3-o-tolyl-1-tosylaziridine (5b). cis-isomer; white solid; mp 202 °C; H-NMR (200 MHz,
CDCl ) δ 2.13 (s, 3H), 2.45 (s, 3H), 4.28 (d, 1H, J = 7.3 Hz), 4.33 (d, 1H, J = 7.3 Hz), 6.91–7.14 (m,
H), 7.22 (d, 2H, J = 8.6 Hz), 7.38 (d, 2H, J = 7.8 Hz), 7.87–7.99 (m, 4H). C-NMR (50 MHz,
CDCl ) δ 21.6, 21.7, 45.6, 47.9, 123.0, 125.6, 127.9, 128.0, 128.2, 129.7, 129.8, 130.0, 131.5, 134.4,
3
H
1
3
4
3
C
1
1
34.5, 135.9, 139.6, 145.2. trans-isomer; white solid; mp 161 °C; H-NMR (200 MHz, CDCl
3 H
) δ 2.38
(
s, 3H), 2.41 (s, 3H), 4.20 (d, 1H, J = 4.7 Hz), 4.35 (d, 1H, J = 4.7 Hz), 7.17–7.28 (m, 6H), 7.59–7.66
1
3
(
m, 4H), 8.21 (d, 2H, J = 8.7 Hz). C-NMR (50 MHz, CDCl ) δ 18.8, 21.6, 45.6, 47.8, 123.0, 125.6,
3 C
127.9, 128.0, 128.1, 128.1, 129.0, 129.7, 129.9, 134.3, 135.9, 139.5, 145.2, 147.3. Anal. Calcd for
22 20 2 4
C H N O
S: C, 64.69; H, 4.94; N, 6.86; S, 7.85. Found: C, 64.79; H, 4.97; N, 6.85; S, 7.92.
1
2
-(2-Chlorophenyl)-3-(4-nitrophenyl)-1-tosylaziridine (5c). cis-isomer; white solid; mp 193 °C; H-NMR
200 MHz, CDCl ) δ 2.45 (s, 3H), 3.39 (d, 1H, J = 7.6 Hz), 3.46 (d, 1H, J = 7.6 Hz), 7.04–7.20 (m,
H), 7.26 (d, 2H, J = 8.6 Hz), 7.38 (d, 2H, J = 8.2 Hz), 7.93 (d, 2H, J = 8.6 Hz), 7.97 (d, 2H, J = 8.2 Hz).
(
3
H
4
1
3
C-NMR (50 MHz, CDCl
3
) δ
C
21.6, 46.0, 46.9, 123.1, 126.5, 128.0, 128.3, 129.0, 129.3, 129.4, 129.5,
1
1
30.0, 133.2, 134.1, 139.1, 145.3, 147.4. trans-isomer; white solid; mp 185 °C; H-NMR (200 MHz,
CDCl ) δ 2.42 (s, 3H), 4.10 (d, 1H, J = 4.5 Hz), 4.56 (d, 1H, J = 4.5 Hz), 7.22–7.41 (m, 6H), 7.69
3
H
1
3
(
d, 2H, J = 8.7 Hz), 7.73 (d, 2H, J = 8.7 Hz), 8.23 (d, 2H, J = 8.7 Hz). C-NMR (50 MHz, CDCl
3
)
δ
C
21.6, 47.2, 49.8, 123.5, 127.0, 127.7, 128.4, 129.4, 129.6, 130.0, 130.0, 131.2, 134.5, 136.1, 139.5,
1
44.8, 148.1. Anal. Calcd for C21
.99; N, 6.43; S, 7.49.
H17ClN
2
O
4
S: C, 58.81; H, 4.00; N, 6.53; S, 7.48. Found: C, 58.88; H,
3
1
2
-(3-Fluorophenyl)-3-(4-nitrophenyl)-1-tosylaziridine (5e). cis-isomer; white solid; mp 108 °C; H-NMR
(200 MHz, CDCl
3
) δ
H
2.47 (s, 3H), 4.22 (d, 1H, J = 9.4Hz), 4.32 (d, 1H, J = 9.4Hz), 6.69–6.88 (m,
3
7
H), 7.04–7.16 (m, 1H), 7.23 (d, 2H, J = 8.3 Hz), 7.39 (d, 2H, J = 8.3 Hz), 7.96 (d, 2H, J = 8.3 Hz)
1
3
3 C
.99 (d, 2H, J = 8.3 Hz). C-NMR (50 MHz, CDCl ) δ 21.7, 46.3, 47.1 (d, J = 2.6 Hz), 114.5 (d,
J = 22.7 Hz), 115.2 (d, J = 21.1 Hz) 123.2 (d, J = 2.9 Hz), 123.3, 128.0, 128.5, 129.9, 130.1, 133.7 (d,
J = 8.0 Hz), 134.2, 139.1, 145.4, 147.6, 162.4 (d, J = 247.0 Hz). trans-isomer; white solid; mp 143 °C;
1
H-NMR (200 MHz, CDCl
3 H
) δ 2.41 (s, 3H), 4.22 (d, 1H, J = 4.4 Hz), 4.26 (d, 1H, J = 4.4 Hz), 7.70
(
d, 2H, J = 8.8 Hz), 7.24–7.41 (m, 4H), 7.60 (d, 2H, J = 8.8 Hz), 7.67 (d, 2H, J = 8.2 Hz), 8.21 (d, 2H,
1
3
J = 8.8 Hz). C NMR (50 MHz, CDCl
3
) δ
16.1 (d, J = 21.2 Hz), 123.7, 124.0 (d, J = 2.9 Hz), 127.5, 129.2, 129.7, 130.0, 134.7 (d, J = 7.7 Hz),
36.4, 140.2, 144.7, 148.1, 162.7 (d, J = 247.4Hz). Anal. Calcd for C21 S: C, 61.16; H, 4.15;
C
21.6, 49.0, 50.1 (d, J = 2.2 Hz), 115.2 (d, J = 22.7 Hz),
1
1
2 4
H17FN O
N, 6.79; S, 7.77. Found: C, 60.51; H, 4.19; N, 6.62; S, 7.66.
2
-(4-Nitrophenyl)-3-(3-(trifluoromethyl)phenyl)-1-tosyl-aziridine (5f). cis-isomer; white solid; mp 63 °C;
1
H-NMR (200 MHz, CDCl
3 H
) δ 2.44 (s, 3H), 4.30 (d, 1H, J = 7.7 Hz), 4.34 (d, 1H, J = 7.7 Hz), 7.21–7.41
1
3
(
m, 8H), 7.95 (d, 2H, J = 8.4 Hz), 7.99 (d, 2H, J = 8.4 Hz). C-NMR (50 MHz, CDCl ) δ 21.6, 46.4,
3 C
46.9, 123.3, 124.4 (q, J = 4.0 Hz), 125.0 (q, J = 4.0 Hz), 128.0, 128.5, 128.8, 130.0, 130.5 (q, J = 33.0 Hz),
1
30.7, 132.3, 133.9, 138.9, 142.5 (q, J = 238.9 Hz), 145.6, 147.5. trans-isomer; white solid; mp 164 °C;
1
H-NMR (200 MHz, CDCl
.20–7.25 (m, 4H), 7.54–7.65 (m, 4H), 7.97 (d, 2H, J = 8.8 Hz), 8.20 (d, 2H, J = 8.8 Hz). C-NMR
50 MHz, CDCl ) δ 21.5, 48.5, 50.1, 123.7, 125.3 (q, J = 3.7Hz), 125.8 (q, J = 3.7 Hz), 127.5, 129.1,
3 H
) δ 2.40 (s, 3H), 4.25 (d, 1H, J = 4.3 Hz), 4.35 (d, 1H, J = 4.3 Hz),
13
7
(
3
C