NH 2 ·HOTf A 4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,0 0,0 5 10 15 20 25 30 35 40 45 50 55 60 65 70 75 80 83,3 cm-1 %T IR spectrum of A (Nujol, cm -1 )
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NH2·HOTfA
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
83,3
cm-1
%T
IR spectrum of A (Nujol, cm-1)
1H NMR spectrum of A (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of A (DMSO-d6, 25 ºC)
NH2·HOTfB
CO2MeH
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 450,00,0
5
10
15
20
25
30
35
40
45
50
55
60
64,5
cm-1
%T
IR spectrum of B (Nujol, cm-1)
1H NMR spectrum of B (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of C (DMSO-d6, 25 ºC)
NHMe·HOTf
C
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
84,9
cm-1
%T
IR spectrum of C (Nujol, cm-1)
1H NMR spectrum of C (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of C (DMSO-d6, 25 ºC)
NH2Pd
AcO 2
1a-OAc
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
81,2
cm-1
%T
IR spectrum of 1a-OAc (Nujol, cm-1)
1H NMR spectrum of 1a-OAc (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 1a-OAc (DMSO-d6, 25 ºC)
NH2Pd
Cl 2
1a-Cl
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
9092,5
cm-1
%T
IR spectrum of 1a-Cl (Nujol, cm-1)
1H NMR spectrum of 1a-Cl (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 1a-Cl (DMSO-d6, 25 ºC)
NH2Pd
Br 2
1a-Br
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
90
95,9
cm-1
%T
IR spectrum of 1a-Br (Nujol, cm-1)
1H NMR spectrum of 1a-Br (DMSO-d6, 25 ºC)
NH2Pd
I 21a-I
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
89,6
1/cm
%T
IR spectrum of 1a-I (Nujol, cm-1)
1H NMR spectrum of 1a-I (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 1a-I (DMSO-d6, 25 ºC)
NH2Pd
Cl 21b-Cl
CO2MeH
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 450,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70,7
cm-1
%T
IR spectrum of 1b-Cl (Nujol, cm-1)
1H NMR spectrum of 1b-Cl (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 1b-Cl (DMSO-d6, 25 ºC)
NH2Pd
I 21b-I
CO2MeH
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
69,3
1/cm
%T
IR spectrum of 1b-I (Nujol, cm-1)
1H NMR spectrum of 1b-I (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 1b-I (DMSO-d6, 25 ºC)
NHMePd
Cl 2
1c-Cl
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
8586,8
cm-1
%T
IR spectrum of 1c-Cl (Nujol, cm-1)
1H NMR spectrum of 1c-Cl (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 1c-Cl (DMSO-d6, 25 ºC)
NHMePd
Br 2
1c-Br
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
90
9596,9
cm-1
%T
IR spectrum of 1c-Br (Nujol, cm-1)
1H NMR spectrum of 1c-Br (CDCl3 + TMS, 25 ºC)
NHMePd
I 21c-I
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
84,3
1/cm
%T
IR spectrum of 1c-I (Nujol, cm-1)
1H NMR spectrum of 1c-I (DMSO-d6, 25 ºC)
13C NMR spectrum of 1c-I (DMSO-d6, 25 ºC)
PdN
I 2
CMe2
2
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
90
95
98,7
cm-1
%T
IR spectrum of 2 (Nujol, cm-1)
1H NMR spectrum of 2 (DMSO-d6, 25 ºC)
13 C APT NMR spectrum of 2 (DMSO-d6, 25 ºC)
PdNH2
PhosS Cl
3a-Cl
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
88,0
cm-1
%T
IR spectrum of 3a-Cl (Nujol, cm-1)
1H NMR spectrum of 3a-Cl (CD2Cl2, 25 ºC)
3a-Br
PdNH2
PhosS Br
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
90
95
100
105107,0
cm-1
%T
IR spectrum of 3a-Br (Nujol, cm-1)
1H NMR spectrum of 3a-Br (CD2Cl2, 25 ºC)
NH2Pd
PhosS I3b-I
CO2MeH
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
76,1
1/cm
%T
IR spectrum of 3b-I (Nujol, cm-1)
1H NMR spectrum of 3b-I (CDCl3 + TMS, 25 ºC)
PdN
Ph3P I
CMe2
4
4000,0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 200,00,0
5
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80
85
90
95
100
105
110
115117,5
cm-1
%T
IR spectrum of 4 (Nujol, cm-1)
1H NMR spectrum of 4 (CDCl3 + TMS, 25 ºC)
13 C APT NMR spectrum of 4 (CDCl3+ TMS, 25 ºC)
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