224
M. Shi, Y. Chen / Journal of Fluorine Chemistry 122 (2003) 219–227
6
7
4
2
1
1
.74 (s, 1H, Ar), 6.90–6.92 (d, 1H, J ¼ 7:5 Hz, Ar), 7.10–
3.1.4.6. [N,N-di-(1,1-diphenyl-1-butenyl)-2,6-(dibro-
mo)]aniline (3f). 3f was obtained as colorless oil, yield 81%,
.41 (m, 11H, Ar); 13C NMR (75 MHz, CDCl ) d 29.810,
3
ꢀ
1
3.886, 109.788, 111.494, 113.878, 123.749 (q, J ¼
71:4 Hz), 125.802, 127.274, 127.392, 127.452, 128.366,
28.584, 129.796, 129.942, 130.059 (q, J ¼ 31:6 Hz),
IR (neat): n 3054, 2986, 1738, 1601, 1494, 1443, 1424 cm ;
1
H NMR (300 MHz, CDCl ) d 2.24–2.32 (m, 4H, CH ), 3.23
3
2
(t, 4H, J ¼ 7:4 Hz, CH ), 6.11(t, 2H, J ¼ 7:5 Hz, ¼CH), 6.79
2
1
3
39.868, 143.543, 145.976, 149.833; MS (EI) m/z: 367
(t, 1H, J ¼ 8:3 Hz, Ar), 7.09–7.47 (m, 22H, Ar); C NMR
þ
(M , 1.75), 174 (100), 145 (9.25), 91 (6.68), 77 (3.25);
HRMS (EI) Calcd. for C H F N 367.1548, Found:
3
(75 MHz, CDCl ) d 29.760, 53.063, 126.794, 126.862,
3
127.135, 127.184, 127.287, 127.381, 128.012, 128.068,
129.788, 133.065, 139.934, 142.509, 142.599, 146.770; MS
2
3 20 3
67.1526.
þ
(
EI) m/z: 663 (M , 0.78), 470 (51.58), 167 (67.24), 129 (100),
3
.1.4.3. [N,N-di-(1,1-diphenyl-1-butenyl)-3-fluoro]aniline
3b). 3b was obtained as colorless oil, yield 61%. IR (neat):
91 (87.64), 77 (9.95); HRMS (EI) Calcd. for C H Br N:
23 20 2
(
467.9962, Found: 467.9944 ([M ꢀ 193:1017]þ).
n 3079, 3055, 3022, 2969, 2885, 1618, 1598, 1576, 1497,
ꢀ1
1
1
2
6
6
443, 1265, 1154, 822 cm ; H NMR (300 MHz, CDCl ) d
3.1.4.7. [N,N-di-(1,1-di-p-tolyl-1-butenyl)-3-(trifluoro-
methyl)]aniline (3i). 3i was obtained as colorless oil, yield
85%; IR (neat): n 3023, 2922, 2851, 1609, 1584, 1508, 1454,
3
.28–2.36 (m, 4H, CH ), 3.22 (t, 4H, J ¼ 7:4 Hz, CH ),
2
2
.06 (t, 2H, J ¼ 7:8 Hz, ¼CH), 6.08–6.14 (m, 2H, Ar),
.24–6.30 (m, 1H, Ar); 6.91–6.99 (m, 1H, Ar), 7.12–7.37
ꢀ1
1
1322 cm ; H NMR (300 MHz, CDCl ) d 2.22 (s, 6H,
3
(
m, 20H, Ar); 13C NMR (75 MHz, CDCl ) d 27.882,
CH ), 2.28 (s, 6H, CH ) 2.29–2.37 (m, 4H, CH ), 3.26 (t, 4H,
J ¼ 7:4 Hz, CH ), 5.99 (t, 2H, J ¼ 7:8 Hz, ¼CH), 6.38–6.41
3
3
3
2
5
Hz), 107.058, 125.758, 127.443, 127.504, 127.562,
1
1
1
3
1.059, 98.985 (d, J ¼ 25:2 Hz), 102.397 (d, J ¼ 20:4
2
(m, 1H, Ar), 6.69 (s, 1H, Ar), 6.80 (d, 1H, J ¼ 7:8 Hz,
1
3
28.531, 128.727, 130.039, 130.503 (d, J ¼ 10:2 Hz),
40.056, 142.484, 144.348, 149.541 (d, J ¼ 9:0 Hz),
Ar), 6.99–7.12 (m, 17H, Ar); C NMR (75 MHz, CDCl )
3
d 21.498, 21.655, 27.846, 51.118, 108.289, 112.334, 115.080,
124.582, 127.034 (q, J ¼ 271:7 Hz), 127.472, 129.309,
129.461, 129.922, 129.974, 131.844 (q, J ¼ 31:4 Hz),
137.109, 137.251, 137.286, 140.005, 144.348, 148.013;
þ
64.619 (d, J ¼ 240:2 Hz); MS (EI) m/z: 523 (M , 1.98),
30 (61.92), 167 (100), 129 (71.14), 91 (73.30); HRMS (EI)
Calcd. for C H FN: 330.1658, Found: 330.1707
2
3 21
[M ꢀ 193:1017]þ).
MS (EI) m/z: 629 (M , 0.26), 408 (12.86), 195 (100),
143 (39.03), 105 (35.57), 91 (4.71); HRMS (EI) Calcd.
þ
(
3
.1.4.4. 1-(1,1-Diphenyl-1-butenylamino)-3-fluorobenzene
for C H F N: 408.1939, Found: 408.1942 ([M ꢀ
2
6 25 3
þ
(
4b). 4b was obtained as colorless oil, yield 16%, IR (neat): n
193:1017] ).
3
1
2
6
6
057, 2960, 2929, 1713, 1621, 1591, 1511, 1497, 1442,
ꢀ
1
1
266 cm ; H NMR (300 MHz, CDCl ) d 2.40–2.47 (m,
3.1.4.8. [N,N-di-(1,1-di-p-methoxyphenyl-1-butenyl)-3-
(trifluoromethyl)]aniline (3j). 3j was obtained as colorless
oil, yield 74%. IR (neat): n 2956, 2934, 2836, 1646, 1606,
3
H, CH ), 3.20 (t, 2H, J ¼ 7:1 Hz, CH ), 3.78 (s, 1H, NH),
2
2
.11 (t, 1H, J ¼ 7:5 Hz, ¼CH), 6.20–6.25 (m, 1H, Ar), 6.21–
.31 (m, 1H, Ar), 6.32–6.39 (m, 1H, Ar), 7.05–7.07 (m, 1H,
ꢀ1
1
1515, 1462, 1200, 1120 cm ; H NMR (300 MHz, CDCl )
d: 2.31–2.38 (m, 4H, CH ), 3.29 (t, 4H, J ¼ 7:4 Hz, CH ),
3
Ar), 7.16–7.38 (m, 10H, Ar); 13C NMR (75 MHz, CDCl ) d
3
2
2
3
0.538, 43.952, 100.558 (d, J ¼ 22:7 Hz), 105.099 (d,
3.76 (s, 6H, OCH ), 3.79 (s, 6H, OCH ), 5.93 (t, 2H,
3 3
J ¼ 21:6 Hz), 108.337, 125.744, 125.955, 127.390,
J ¼ 7:8 Hz, ¼CH), 6.43–6.46 (m, 1H, Ar), 6.71 (s, 1H,
1
27.435, 128.381, 128.589, 129.962, 130.565 (d, J ¼ 9:2
Ar), 6.78–6.88 (m, 9H, Ar), 7.01–7.16 (m, 9H, Ar); 13
C
Hz), 140.169, 142.581, 144.197, 149.167 (d, J ¼ 9:5 Hz),
NMR (75 MHz, CDCl ) d 27.342, 50.587, 55.163, 55.351,
3
þ
1
1
60.484 (d, J ¼ 248:6 Hz). MS (EI) m/z: 317 (M , 7.60),
107.585, 111.559, 113.377, 113.552, 114.420, 123.269,
124.469 (q, J ¼ 271:5 Hz), 128.157, 130.659, 131.238 (q,
24 (100), 91 (4.10), 77 (2.35); HRMS (EI) Calcd. for
C H FN: 317.1580, Found: 317.1593.
22 20
J ¼ 31:6 Hz), 132.028, 132.180, 135.126, 142.950,
þ
1
47.596, 158.528, 158.759; MS (EI) m/z: 244 (M , 1.85),
3.1.4.5. [N,N-di-(1,1-diphenyl-1-butenyl)-3,5-(dichloro)]-
aniline (3e). 3e was obtained as colorless oil, yield 93%. IR
440 (10.31), 227 (100), 167 (30.58), 129 (29.26), 91 (27.20);
HRMS (EI) Calcd. for C H F NO : 440.1837, Found:
2
6
25
3
2
(
neat): n 3080, 3053, 3024, 2985, 1738, 1626, 1587, 1551,
440.1850 ([M ꢀ 193:1017]þ).
ꢀ
1
1
1
492, 743 cm ; H NMR (300 MHz, CDCl ) d 2.27–2.34
3
(
m, 4H, CH ), 3.20 (t, 4H, J ¼ 7:3 Hz, CH ), 6.01 (t, 2H,
3.1.4.9. [N,N-di-(1-o-chlorophenyl-1-phenyl-1-butenyl)-3-
(trifluoromethyl)]aniline (3k). 3k was obtained as colorless
oil, yield 21%. IR (neat): n 3062, 2917, 2865, 1623,
2
2
J ¼ 7:7 Hz, ¼CH), 6.31 (s, 2H, Ar), 6.57 (s, 1H, Ar), 7.09–
7
5
1
1
3
.37 (m, 20H, Ar); 13C NMR (75 MHz, CDCl ) d 27.341,
0.462, 109.854, 115.384, 124.801, 127.077, 127.118,
3
ꢀ
1
1
1599, 1499 cm ; H NMR (300 MHz, CDCl ) d 2.20–
3
27.188, 128.127, 128.357, 129.465, 135.424, 139.442,
þ
2.25 (m, 4H, CH ), 3.32 (t, 4H, J ¼ 7:5 Hz, CH ), 6.23
2
2
41.935, 144.148, 148.073; MS (EI) m/z: 573 (M , 2.75),
80 (54.45), 167 (100), 129 (48.45), 91 (34.76); HRMS
(t, 2H, J ¼ 7:7 Hz, ¼CH), 6.42–6.79 (m, 4H, Ar), 7.05–
1
3
7.44 (m, 18H, Ar); C NMR (75 MHz, CDCl ) d 27.393,
3
(
(
EI) Calcd. for C H Cl N: 380.0973, Found: 380.1003
20
43.433, 106.291, 108.890, 111.199, 116.960, 125.111
(q, J ¼ 270:8 Hz), 126.404, 126.453, 127.661, 128.537,
2
3
2
[M ꢀ 193:1017]þ).