1202
H. Wang et al. / Journal of Fluorine Chemistry 127 (2006) 1195–1203
3H), 3.30 (1H, A part of a AB-d system, J = 6.3, JAB = 15.6),
3.17 (1H, B part of a AB-d system, J = 1.8, JBA = 15.6), 2.62 (t,
J = 7.5, 2H), 2.34–2.12 (m, 2H); dC (in CDCl3) 9.95 (t,
4.17. 2-(1,1-Difluoro-3-phenyl-propyl)-1-(4-methoxy-
phenyl)-azetidine (7f)
J
CF = 5.7), 29.32 (t, JCF = 4.2), 38.64, 53.611 (t, JCF = 35.09),
114.5, 118.0, 119.6, 121.4 (t, JCF = 245.80), 129.8, 157.0,
162.9; dF (in CDCl3) ꢁ105.3 (1F, A part of a AB-d system,
J
AB = 251.3), ꢁ107.7 (1F, B part of a AB-d system,
J
BA = 251.3); MS (EI): m/z (%) = 280 (M+, 15), 238 (16),
149 (22), 134 (100), 77 (37), 69 (3).
The product, a colorless solid, was isolated in 76%
(yield); mp: 108–110 8C; [Found (ES): 331.1396,
C19H19F2NO2 requires 331.1384]; nmax (KBr)/cmꢁ1 3478,
3026, 2926, 1784, 1513, 1386, 1242, 698; dH (in CDCl3)
7.44–6.90 (m, 9H), 4.41–4.37 (m, 1H), 3.81 (s, 3H), 3.22
(1H, A part of a AB-d system, J = 6.0, JAB = 15.3), 3.03 (1H,
B part of a AB-d system, J = 2.4, JBA = 15.3), 2.91 (t, J = 8.1,
2H), 2.27–2.13 (m, 2H); dC (in CDCl3) 27.3 (t, JCF = 4.59),
35.1 (t, JCF = 24.10), 38.7, 54.04 (t, JCF = 30.72), 55.5,
114.4, 119.7, 122.7 (t, JCF = 196.16), 126.5, 127.7, 128.3,
130.7, 139.9, 156.8, 163.5; dF (in CDCl3) ꢁ105.3 (1F, A part
of a AB-d system, JCF = 253.0), ꢁ106.2 (1F, B part of
a AB-d system, JCF = 252.4); MS (EI): m/z (%) = 331
(M+, 100), 225 (67), 185 (46), 170 (8), 134 (22), 91 (16),
77 (6).
4.15. 5,5-Difluoro-5-[1-(4-methoxy-phenyl)-azetidin-2-yl]-
pentan-2-one (7d)
The product, a colorless solid, was isolated in 21% (yield);
mp: 122–124 8C; [Found (ES): 297.1193, C15H17F2NO3
requires 297.1176]; nmax (KBr)/cmꢁ1 3476, 2969, 2937,
2842, 1742, 1716, 1515, 1380, 841; dH (in CDCl3) 7.37–7.33
(m, 2H), 6.90–6.84 (m, 2H), 4.39–4.32 (m, 1H), 3.78 (s, 3H),
3.69 (s, 3H), 3.23(1H, A part of a AB-d system, J = 6.0,
J
AB = 15.3), 3.00 (1H, B part of a AB-d system, J = 3.0,
BA = 15.3), 2.70 (t, J = 7.2, 2H), 2.22–2.10 (m, 3H); dC (in
CDCl3) 26.8 (t, JCF = 23.87), 30.0, 34.8, 38.7, 54.0 (t,
CF = 29.52), 55.5, 114.3, 119.6 (t, JCF = 244.20), 130.5,
J
4.18. 4-(1,1-Difluoro-but-3-enyl)-1-(4-methoxy-phenyl)-
azetidin-2-one (8)
J
156.7, 163.4, 206.0; dF (in CDCl3) ꢁ105.2 (1F, A part of a
AB-d system, JCF = 249.3), ꢁ106.9 (1F, B part of a AB-d
system, JCF = 251.3); MS (EI): m/z (%) = 297 (M+, 91), 191
(43), 149 (22),134 (100), 77 (15).
4.16. 2-(3-Ethoxy-1,1-difluoro-propyl)-1-
(4-methoxy-phenyl)-azetidine (7e)
The product, a colorless solid, was isolated in 25%
(yield); mp: 52–54 8C; (Found: C, 62.91; H, 5.73; N, 5.23.
Calc. for C13H16O3BrF2N: C, 62.91; H, 5.66; N, 5.24%);
nmax (KBr)/cmꢁ1 3484, 2967, 2957, 2843, 1760, 1512, 1384,
1115, 831; dH (in CDCl3) 7.41–7.35 (m, 2H), 6.91–6.86(m,
2H), 5.89(m, 1H), 5.27 (m, 2H), 4.42–4.34 (m, 1H), 3.80 (s,
3H), 3.21 (1H, A part of a AB-d system, J = 6.0, JAB = 15.3),
3.03 (1H, B part of a AB-d system, J = 2.7, JBA = 15.3),
2.74–2.60 (m, 2H), 2.33-2.12 (m, 2H); dC (in CDCl3) 38.2,
38.7 (m), 53.7 (t, JCF = 30.35), 55.5, 114.3, 119.8, 121.5,
121.9 (t, JCF = 244.8), 127.6, 130.6, 156.8, 163.4; dF (in
CDCl3) ꢁ102.9 (1F, A part of a AB-d system, 253.5), ꢁ104.5
(1F, B part of a AB-d system, J = 252.7); MS (EI): m/z
(%) = 267 (M+, 100), 225 (25), 204 (48), 160 (4), 149 (18),
134 (89), 77 (17).
The product, a pale yellow oil was isolated in 17% (yield);
[Found (ES): 299.1287, C15H19F2NO3 requires 299.1333]; nmax
(KBr)/cmꢁ1 2974, 2877, 1762, 1514, 1382, 1247, 1117; dH (in
CDCl3) 7.42–6.90 (m, 2H), 6.90–6.85 (m, 2H), 4.55–4.46 (m,
1H), 3.80 (s, 3H), 3.68–3.60 (m, 2H), 3.54–3.47 (m, 2H), 3.19
(1H, A part of a AB-d system, J = 5.7, JAB = 15.6), 3.00 (1H, B
part of a AB-d system, J = 3.0, JBA = 15.6), 2.27–2.12 (m, 2H),
1.30–1.19 (m, 3H); dC (in CDCl3) 15.06, 29.69, 34.66 (t,
J
CF = 39.61), 38.73 (t, JCF = 4.07), 54.02 (t, JCF = 28.76),
63.56, 66.58, 114.26, 119.9, 122.5 (t, JCF = 244.05), 130.8,
156.7, 163.7; dF (in CDCl3) ꢁ103.0 (1F, A part of a AB-d
system, JCF = 248.4), ꢁ106.8 (1F, B part of a AB-d system,
Acknowledgement
J
CF = 254.4); MS (EI): m/z (%) = 299 (M+, 100), 193 (29), 185
The authors thank the National Natural Science Foundation
of China (NNSFC) (Nos. 20372077 and 20472106).
(100), 176 (15), 149 (34), 134 (60), 77 (13).