Paper
Yield 85%; brick red solid; mp. 114–115 °C; H NMR (CDCl
Dalton Transactions
1
3
,
71.9, 79.8, 114.3, 117.5, 118.4, 124.7, 126.5, 128.4, 129.4, 130.6,
5
13
3
00 MHz): δ 4.03 (s, 4H, H ), 4.17 (s, 10H, H ), 4.36 (s, 4H, 132.5, 133.3, 134.6, 135.5, 135.7, 138.1, 138.6, 139.8, 143.2,
7
12
8
11
H ), 4.45 (s, 4H, H ), 4.51–4.54 (m, 4H, H ), 4.57 (s, 4H, H ), 146.7, 161.2, 188.3. HRMS (ESI-micrOTOF-QII) calcd for
2
+
4
.77 (dd, J = 5.7 Hz, 7.2 Hz, 1H, H ), 4.95 (d, J = 5.1 Hz, 1H,
C
67
H
61FFe
3-[Bis-(1-{3-[4-(3-ferrocenyl-acryloyl)-phenoxy]-propyl}-1H-
H, H ), 6.90 (d, J = 8.6 Hz, 4H, –ArH), 7.08 (d, J = 15.9 Hz, 2H, [1,2,3]triazol-4-ylmethyl)-amino]-4-styryl-1-p-tolyl-azetidin-2-one
2 8 5
N O [M + H] 1189.2590, found 1189.2584.
1
3
H ), 6.23 (dd, J = 7.2 Hz, 15.9 Hz, 1H, H ), 6.75 (d, J = 15.9 Hz,
1
4
9
10
1
H ), 7.23–7.37 (m, 10H, –ArH), 7.73 (d, J = 15.9 Hz, 2H, H ), (10h). Yield 80%; brick red solid; mp. 104–105 °C; H NMR
7
6
13
8
.87 (s, 2H, triazole-H ), 7.98 (d, J = 8.4 Hz, 4H, –ArH);
C
(CDCl , 300 MHz): δ 1.91–2.24 (m, 2H, H ), 2.35 (s, 3H, –CH ),
3 3
5
13
7
14
NMR (CDCl
3
, 75 MHz): 49.6, 58.7, 60.3, 66.7, 69.5, 69.6, 71.4, 4.02 (s, 4H, H ), 4.14 (s, 10H, H ), 4.45 (s, 8H, H + H ), 4.51
1
2
1
9
7
1
1
C
6.6, 79.3, 114.7, 117.2, 118.7, 126.2, 126.4, 126.7, 128.1, 128.4, (s, 4H, H ), 5.12–5.28 (m, 5H, H + H ), 5.76 (dd, J = 7.2 Hz,
28.9, 129.4, 129.9, 130.8, 131.7, 132.8, 134.6, 136.4, 146.6, 15.9 Hz, 1H, H ), 6.24 (dd, J = 5.7 Hz, 7.2 Hz, 1H, H ), 6.74 (d,
3
2
4
46.8, 161.7, 188.9. HRMS (ESI-micrOTOF-QII) calcd for J = 15.9 Hz, 1H, H ), 6.89–6.97 (m, 5H, –ArH), 7.14 (d, J =
+
10
65
H
58Fe
2
N
8
O
5
[M + H] 1143.6244, found 1143.6437.
15.9 Hz, 2H, H ), 7.25–7.56 (m, 8H, –ArH), 7.73 (d, J = 15.9
1
1
6
3-[Bis-(1-{2-[4-(3-ferrocenyl-acryloyl)-phenoxy]-ethyl}-1H-[1,2,3]- Hz, 2H, H ), 7.91 (s, 2H, triazole-H ), 7.93 (d, J = 9.0 Hz, 4H,
1
3
triazol-4-ylmethyl)-amino]-1-cycloheptyl-4-styryl-azetidin-2-one –ArH); C NMR (CDCl
3
, 75 MHz): 19.3, 21.5, 47.4, 58.5, 60.1,
10e). Yield 78%; brick red solid; mp. 102–103 °C; H NMR 64.8, 69.2, 69.5, 71.7, 71.9, 79.6, 114.4, 115.7, 116.6, 118.2,
CDCl , 300 MHz): δ 1.34–2.24 (m, 12H, cycloheptyl); 3.51–3.56 118.8, 122.2, 124.2, 126.1, 126.3, 128.6, 128.8, 130.7, 131.6,
1
(
(
(
3
5
13
m, 1H, cycloheptyl H), 4.03 (s, 4H, H ), 4.18 (s, 10H, H ), 4.35 132.3, 135.4, 136.4, 143.1, 146.4, 161.5, 188.5. HRMS (ESI-
7
12
8
+
(
4
5
s, 4H, H ), 4.46 (s, 4H, H ), 4.52–4.55 (m, 4H, H ), 4.55 (s, micrOTOF-QII) calcd for C68
H
64Fe
2
N
8
O
5
[M + H] 1185.6373,
1
1
2
H, H ), 4.73 (dd, J = 5.7 Hz, 7.2 Hz, 1H, H ), 4.95 (d, J = found 1185.6369.
.1 Hz, 1H, H ), 6.25 (dd, J = 7.2 Hz, 15.9 Hz, 1H, H ), 6.66 (d,
J = 15.9 Hz, 1H, H ), 6.90 (d, J = 8.6 Hz, 4H, –ArH), 7.10 (d, J = triazol-4-ylmethyl)-amino]-1-(4-chloro-phenyl)-4-styryl-azetidin-
5.9 Hz, 2H, H ), 7.23–7.32 (m, 5H, –ArH), 7.75 (d, J = 15.9 Hz, 2-one (10i). Yield 84%; brick red solid; mp. 101–102 °C; H
H, H ), 7.83 (s, 2H, triazole-H ), 7.95 (d, J = 8.6 Hz, 4H, NMR (CDCl , 300 MHz): δ 2.33–2.39 (m, 4H, H ), 4.04 (s, 4H,
3
ArH); C NMR (CDCl
1
3
3-[Bis-(1-{3-[4-(3-ferrocenyl-acryloyl)-phenoxy]-propyl}-1H-[1,2,3]-
4
9
1
1
2
–
1
0
6
8
1
3
5
13
7
14
12
3
, 75 MHz): 23.5, 28.7, 32.6, 48.8, 49.5, H ), 4.12 (s, 10H, H ), 4.45 (s, 8H, H + H ), 4.56 (s, 4H, H ),
1
9
5
1
1
8.7, 60.1, 66.4, 69.3, 69.7, 71.0, 76.2, 79.5, 114.6, 117.1, 118.3, 5.11–5.31 (m, 5H, H + H ), 5.81(dd, J = 5.7 Hz, 7.2 Hz, 1H,
26.3, 126.5, 126.6, 128.1, 129.3, 131.4, 132.2, 134.6, 136.8, H ), 6.21 (dd, J = 7.2 Hz, 15.9 Hz, 1H, H ), 6.78 (d, J = 15.9 Hz,
2
3
4
46.1, 146.5, 161.6, 188.7. HRMS (ESI-micrOTOF-QII) calcd for 1H, H ), 6.86–6.97 (m, 8H, –ArH), 7.14 (d, J = 15.9 Hz, 2H,
+
10
6
C H Fe N O [M + H] 1162.8946, found 1162.8940.
H ), 7.26–7.55 (m, 5H, –ArH), 7.66 (s, 2H, triazole-H ), 7.74 (d,
6
6
67
2 8 5
1
1
13
3
-[Bis-(1-{2-[4-(3-ferrocenyl-acryloyl)-phenoxy]-ethyl}-1H-[1,2,3]- J = 15.9 Hz, 2H, H ), 7.98 (d, J = 8.9 Hz, 4H, –ArH); C NMR
triazol-4-ylmethyl)-amino]-1-cyclohexyl-4-styryl-azetidin-2-one (CDCl , 75 MHz): 19.3, 45.4, 49.6, 58.5, 62.4, 66.7, 69.3, 69.5,
10f). Yield 81%; brick red solid; mp. 103–104 °C; H NMR 71.8, 79.9, 114.2, 117.4, 118.1, 124.6, 126.4, 128.6, 129.5, 130.3,
CDCl , 300 MHz): δ 1.44–2.23 (m, 10H, cyclohexyl); 3.51–3.53 132.2, 133.7, 134.3, 135.5, 135.7, 138.5, 138.8, 139.6, 143.0,
m, 1H, cyclohexyl H), 4.00 (s, 4H, H ), 4.15 (s, 10H, H ), 4.33 146.5, 161.5, 188.9. HRMS (ESI-micrOTOF-QII) calcd for
3
1
(
(
(
(
4
3
5
13
7
12
8
+
s, 4H, H ), 4.47 (s, 4H, H ), 4.51–4.54 (m, 4H, H ), 4.55 (s, C H ClFe N O [M + H] 1205.8463, found 1205.8459.
67 61 2 8 5
1
1
2
H, H ), 4.75 (dd, J = 5.7 Hz, 7.2 Hz, 1H, H ), 4.96 (d, J =
3-[Bis-(1-{3-[4-(3-ferrocenyl-acryloyl)-phenoxy]-propyl}-1H-
1
3
5
.1 Hz, 1H, H ), 6.27 (dd, J = 7.2 Hz, 15.9 Hz, 1H, H ), 6.62 (d, [1,2,3]triazol-4-ylmethyl)-amino]-1-phenyl-4-styryl-azetidin-2-
4
1
J = 15.9 Hz, 1H, H ), 6.94 (d, J = 8.6 Hz, 4H, –ArH), 7.08 (d, J = one (10j). Yield 78%; brick red solid; mp. 106–107 °C;
1
2
–
H
9
8
3
5.9 Hz, 2H, H ), 7.24–7.36 (m, 5H, –ArH), 7.69 (d, J = 15.9 Hz, NMR (CDCl , 300 MHz): δ 2.29–2.35 (m, 4H, H ), 4.01 (s, 4H,
1
0
6
5
13
7
14
12
H, H ), 7.83 (s, 2H, triazole-H ), 7.96 (d, J = 8.6 Hz, 4H, H ), 4.15 (s, 10H, H ), 4.47 (s, 8H, H + H ), 4.56 (s, 4H, H ),
1
3
1
9
ArH); C NMR (CDCl , 75 MHz): 22.3, 27.6, 31.7, 47.5, 49.8, 5.13–5.26 (m, 5H, H + H ), 5.80 (dd, J = 5.7 Hz, 7.2 Hz, 1H,
3
2
3
5
1
1
C
8.4, 60.3, 66.8, 69.2, 69.7, 71.0, 76.3, 79.6, 114.7, 117.3, 118.4, H ), 6.24 (dd, J = 7.2 Hz, 15.9 Hz, 1H, H ), 6.74 (d, J = 15.9 Hz,
26.2, 126.3, 126.7, 128.2, 129.6, 131.7, 132.6, 134.4, 136.6, 1H, H ), 6.89–6.98 (m, 8H, –ArH), 7.11 (d, J = 15.9 Hz, 2H,
4
1
0
6
46.3, 146.8, 161.1, 188.8. HRMS (ESI-micrOTOF-QII) calcd for H ), 7.24–7.55 (m, 6H, –ArH), 7.65 (s, 2H, triazole-H ), 7.74 (d,
+
11
13
65
H
64Fe
2
N
8
O
5
[M + H] 1148.1147, found 1148.1142.
J = 15.9 Hz, 2H, H ), 7.98 (d, J = 8.9 Hz, 4H, –ArH); C NMR
, 75 MHz): 19.2, 47.5, 58.2, 60.7, 64.3, 69.7, 69.9, 71.5,
3-[Bis-(1-{3-[4-(3-ferrocenyl-acryloyl)-phenoxy]-propyl}-1H-[1,2,3]- (CDCl
3
triazol-4-ylmethyl)-amino]-1-(4-fluoro-phenyl)-4-styryl-azetidin- 71.6, 79.3, 114.1, 115.7, 116.2, 118.6, 118.9, 122.3, 124.5, 126.6,
1
2
-one (10g). Yield 81%; brick red solid; mp. 104–105 °C; H 126.9, 128.1, 128.4, 130.4, 131.2, 132.5, 135.8, 136.8, 143.3,
8
3
NMR (CDCl , 300 MHz): δ 2.32–2.37 (m, 4H, H ), 4.03 (s, 4H, 146.4, 161.1, 188.6. HRMS (ESI-micrOTOF-QII) calcd for
5
13
7
14
12
+
H ), 4.14 (s, 10H, H ), 4.47 (s, 8H, H + H ), 4.57 (s, 4H, H ), C H Fe N O [M + H] 1171.5113, found 1171.5117.
6
7
62
2 8 5
1
9
5
.13–5.29 (m, 5H, H + H ), 5.82 (dd, J = 5.7 Hz, 7.2 Hz, 1H,
H ), 6.22 (dd, J = 7.2 Hz, 15.9 Hz, 1H, H ), 6.76 (d, J = 15.9 Hz, [1,2,3]triazol-4-ylmethyl)-amino]-1-cycloheptyl-4-styryl-azetidin-
H, H ), 6.88–6.99 (m, 8H, –ArH), 7.12 (d, J = 15.9 Hz, 2H, 2-one (10k). Yield 80%; brick red solid; mp. 102–103 °C;
H ), 7.27–7.58 (m, 5H, –ArH), 7.65 (s, 2H, triazole-H ), 7.73 (d,
J = 15.9 Hz, 2H, H ), 7.97 (d, J = 8.9 Hz, 4H, –ArH); C NMR heptyl); 3.54–3.58 (m, 1H, cycloheptyl H), 4.01 (s, 4H, H ), 4.15
CDCl , 75 MHz): 19.5, 45.3, 49.4, 58.6, 62.7, 66.4, 69.1, 69.6, (s, 10H, H ), 4.46 (s, 8H, H + H ), 4.55 (s, 4H, H ),
3-[Bis-(1-{3-[4-(3-ferrocenyl-acryloyl)-phenoxy]-propyl}-1H-
2
3
4
1
1
0
6
1
8
H NMR (CDCl
3
, 300 MHz): δ 1.32–2.32 (m, 16H, H + cyclo-
1
1
13
5
1
3
7
14
12
(
3
1
498 | Dalton Trans., 2013, 42, 1492–1500
This journal is © The Royal Society of Chemistry 2013