royal society of chemistry · vaijinath mane, tarun kumar, sourav pradhan, savita katiyar, irishi...
TRANSCRIPT
1
NMR Spectra
For
One-pot Regioselective Synthesis of Functionalized and Fused Furans from Morita-Baylis-Hillman and Rauhut-Currier Adducts of
Nitroalkenes
Vaijinath Mane, Tarun Kumar, Sourav Pradhan, Savita Katiyar, Irishi N. N.Namboothiri*
Department of Chemistry ,Indian Institute of Technology Bombay, Mumbai 400076, India
E-mail: [email protected]
Entry Table of Contents Page
1 Figure S1. 1H NMR Spectrum of 5a 4
2 Figure S2. 13
C NMR Spectrum of 5a 5
3 Figure S3. 1H-
1H NOESY Spectrum of 5a 6
4 Figure S4. 1H-
1H NOESY Spectrum (Expansion) of 5a 7
5 Figure S5. 1H NMR Spectrum of 5b 8
6 Figure S6. 13
C NMR Spectrum of 5b 9
7 Figure S7. 1H NMR Spectrum of 5c 10
8 Figure S8. 13
C NMR Spectrum of 5c 11
9 Figure S9. 1H NMR Spectrum of 5d 12
10 Figure S10. 13
C NMR Spectrum of 5d 13
11 Figure S11. 1H NMR Spectrum of 5e 14
12 Figure S12. 13
C NMR Spectrum of 5e 15
13 Figure S13.1H NMR Spectrum of 5f 16
14 Figure S14. 13
C NMR Spectrum of 5f 17
15 Figure S15. 1H NMR Spectrum of 5g 18
16 Figure S16. 13
C NMR Spectrum of 5g 19
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015
2
17 Figure S17. 1H NMR Spectrum of 5h 20
18 Figure S18. 13
C NMR Spectrum of 5h 21
19 Figure S19. 1H NMR Spectrum of 5i 22
20 Figure S20. 13
C NMR Spectrum of 3i 23
21 Figure S21. 1H NMR Spectrum of 12a 24
22 Figure S22. 13
C NMR Spectrum of 12a 25
23 Figure S23. 1H-
1H NOESY Spectrum of 12a 26
24 Figure S24. 1H-
1H NOESY Spectrum (Expansion)of 12a 27
25 Figure S25. 1H NMR Spectrum of 12b 28
26 Figure S26. 13
C NMR Spectrum of 12b 29
27 Figure S27. 1H NMR Spectrum of 12c 30
28 Figure S28. 13
C NMR Spectrum of12c 31
29 Figure S29. 1H NMR Spectrum of 12d 32
30 Figure S30. 13
C NMR Spectrum of 12d 33
31 Figure S31. 1H NMR Spectrum of 12e 34
32 Figure S32. 13
C NMR Spectrum of 12e 35
33 Figure S33. 1H NMR Spectrum of 12f 36
34 Figure S34. 13
C NMR Spectrum of 12f 37
35 Figure S35. 1H NMR Spectrum of 12g 38
36 Figure S36. 13
C NMR Spectrum of 12g 39
37 Figure S37. 1H NMR Spectrum of 12h 40
38 Figure S38. 13
C NMR Spectrum of 12h 41
39 Figure S39. 1H NMR Spectrum of 12i 42
40 Figure S40. 13
C NMR Spectrum of 12i 43
41 Figure S41. 1H NMR Spectrum of 12j 44
42 Figure S42. 13
C NMR Spectrum of 12j 45
43 Figure S43. 1H NMR Spectrum of 13a 46
44 Figure S44. 13
C NMR Spectrum of 13a 47
3
45 Figure S45. 1H NMR Spectrum of 13b 48
46 Figure S46. 13
C NMR Spectrum of 13b 49
47 Figure S47. 1H NMR Spectrum of 13c 50
48 Figure S48. 13
C NMR Spectrum of 13c 51
49 Figure S49. 1H NMR Spectrum of 13d 52
50 Figure S50. 13
C NMR Spectrum of 13d 53
51 Figure S51. 1H NMR Spectrum of 13e 54
52 Figure S52. 13
C NMR Spectrum of 13e 55
53 Figure S53. 1H NMR Spectrum of 13f 56
54 Figure S54. 13
C NMR Spectrum of 13f 57
55 Figure S55. 1H NMR Spectrum of 13g 58
56 Figure S56. 13
C NMR Spectrum of 13g 59
57 Figure S57.1H NMR Spectrum of 13h 60
58 Figure S58. 13
C NMR Spectrum of 13h 61
4
Figure S1. 1H NMR Spectrum of 5a
5
Figure S2. 13
C NMR Spectrum of 5a
6
Figure S3. 1H-
1H NOESY Spectrum of 5a
7
Figure S4. 1H-
1H NOESY(Expansion) Spectrum of 5a
8
Figure S5. 1H NMR Spectrum of 5b
9
Figure S6. 13
C NMR Spectrum of 5b
10
Figure S7. 1H NMR Spectrum of 5c
11
Figure S8. 13
C NMR Spectrum of 5c
12
Figure S9. 1H NMR Spectrum of 5d
13
Figure S10. 13
C NMR Spectrum of 5d
14
Figure S11. 1H NMR Spectrum of 5e
15
Figure S12. 13
C NMR Spectrum of 5e
16
Figure S13. 1H NMR Spectrum of 5f
17
Figure S14. 13
C NMR Spectrum of 5f
18
Figure S15. 1H NMR Spectrum of 5g
19
Figure S16. 13
C NMR Spectrum of 5g
20
Figure S17. 1H NMR Spectrum of 5h
21
Figure S18. 13
C NMR Spectrum of 5h
22
Figure S19. 1H NMR Spectrum of 5i
23
Figure S20. 13
C NMR Spectrum of 5i
24
Figure S21. 1H NMR Spectrum of 12a
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
7
2.0
0
1.0
0
0.6
8
1.3
5
0.6
8
0.4
4
1.3
2
Current Data Parameters
NAME inn-mvd-57-1h
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20120927
Time 22.16
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 10
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 32
DW 60.800 usec
DE 6.50 usec
TE 300.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
25
Figure S22. 13
C NMR Spectrum of 12a
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.50
28
.73
29
.99
35
.07
37
.79
41
.78
53
.11
76
.88
77
.20
77
.52
11
8.6
9
11
9.6
2
12
7.4
3
12
8.1
2
12
9.9
0
13
1.3
7
15
1.1
9
16
5.2
2
19
3.6
3
20
7.1
1
Current Data Parameters
NAME inn-mvd-57-13c
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20120927
Time 22.18
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 70
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 300.0 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127550 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
26
Figure S23. 1H-
1H NOESY Spectrum of 12a
ppm
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
Current Data Parameters
NAME INN-MVD-57-noesyEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150420
Time 13.32INSTRUM spectPROBHD 5 mm PABBO BB/
PULPROG noesygpphTD 2048SOLVENT CDCl3NS 8
DS 16SWH 4012.841 HzFIDRES 1.959395 HzAQ 0.2551808 sec
RG 30.72DW 124.600 usecDE 6.50 usec
TE 298.9 K
D0 0.00010815 secD1 2.00000000 secD8 0.80000001 sec
D16 0.00020000 sec
IN0 0.00024940 sec
======== CHANNEL f1 ========
SFO1 500.1321606 MHz
NUC1 1HP1 13.00 usec
P2 26.00 usecPLW1 13.00000000 W
====== GRADIENT CHANNEL =====
GPNAM[1] SMSQ10.100GPZ1 40.00 %
P16 1000.00 usec
F1 - Acquisition parametersTD 322SFO1 500.1322 MHz
FIDRES 12.452246 HzSW 8.017 ppmFnMODE TPPI
F2 - Processing parametersSI 1024SF 500.1300121 MHzWDW QSINE
SSB 2LB 0 HzGB 0
PC 1.00
F1 - Processing parametersSI 1024
MC2 TPPI
SF 500.1300121 MHzWDW QSINESSB 2
LB 0 Hz
GB 0
27
Figure S24. 1H-
1H NOESY Spectrum (Expansion) of 12a
ppm
0.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.93.03.13.2 ppm
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
3.0
Current Data Parameters
NAME INN-MVD-57-noesyEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150420
Time 13.32INSTRUM spectPROBHD 5 mm PABBO BB/
PULPROG noesygpphTD 2048SOLVENT CDCl3NS 8
DS 16SWH 4012.841 HzFIDRES 1.959395 HzAQ 0.2551808 sec
RG 30.72DW 124.600 usecDE 6.50 usec
TE 298.9 K
D0 0.00010815 secD1 2.00000000 secD8 0.80000001 sec
D16 0.00020000 sec
IN0 0.00024940 sec
======== CHANNEL f1 ========
SFO1 500.1321606 MHz
NUC1 1HP1 13.00 usec
P2 26.00 usecPLW1 13.00000000 W
====== GRADIENT CHANNEL =====
GPNAM[1] SMSQ10.100GPZ1 40.00 %
P16 1000.00 usec
F1 - Acquisition parametersTD 322SFO1 500.1322 MHz
FIDRES 12.452246 HzSW 8.017 ppmFnMODE TPPI
F2 - Processing parametersSI 1024SF 500.1300121 MHzWDW QSINE
SSB 2LB 0 HzGB 0
PC 1.00
F1 - Processing parametersSI 1024
MC2 TPPI
SF 500.1300121 MHzWDW QSINESSB 2
LB 0 Hz
GB 0
28
Figure S25. 1H NMR Spectrum of 12b
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
8
1.1
8
0.6
0
1.0
0
0.4
0
0.4
2
0.4
1
0.4
0
0.4
8
Current Data Parameters
NAME INN-MVD-88-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121116
Time 0.36
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 12
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 32
DW 60.800 usec
DE 6.50 usec
TE 293.9 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
29
Figure S26. 13
C NMR Spectrum of 12b
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.53
21
.43
28
.75
30
.00
35
.05
37
.82
41
.84
53
.15
76
.88
77
.20
77
.52
11
8.7
7
11
9.5
4
12
8.3
3
12
8.8
8
12
9.7
6
13
7.1
2
15
0.9
7
16
5.1
3
19
3.6
0
20
7.1
4Current Data Parameters
NAME INN-MVD-88-13C
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121116
Time 0.39
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 107
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 294.4 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127539 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
30
Figure S27. 1H NMR Spectrum of 12c
10 9 8 7 6 5 4 3 2 1 0 ppm
6.0
9
3.0
6
2.0
9
2.0
0
2.0
6
2.0
1
3.1
0
1.0
0
1.0
2
0.9
9
1.1
4
Current Data Parameters
NAME INN-MVD--199-1H
EXPNO 3
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150218
Time 22.53
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 2
SWH 10000.000 Hz
FIDRES 0.152588 Hz
AQ 3.2767999 sec
RG 30.72
DW 50.000 usec
DE 6.50 usec
TE 299.2 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 500.1330885 MHz
NUC1 1H
P1 13.00 usec
PLW1 13.00000000 W
F2 - Processing parameters
SI 65536
SF 500.1300117 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
31
Figure S28. 13
C NMR Spectrum of 12c
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.62
28
.76
30
.02
35
.06
37
.83
41
.77
53
.17
55
.44
76
.95
77
.20
77
.46
11
3.2
5
11
5.6
3
11
9.5
4
12
2.3
5
12
9.0
9
13
2.7
0
15
1.3
2
15
9.3
1
16
5.2
0
19
3.5
4
20
7.0
9
Current Data Parameters
NAME INN-MVD-199-13C
EXPNO 11
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140303
Time 23.27
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 1197
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010048 sec
RG 197.27
DW 16.800 usec
DE 6.50 usec
TE 295.6 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 125.7703637 MHz
NUC1 13C
P1 8.90 usec
PLW1 103.00000000 W
======== CHANNEL f2 ========
SFO2 500.1320005 MHz
NUC2 1H
CPDPRG[2 waltz16
PCPD2 80.00 usec
PLW2 13.00000000 W
PLW12 0.34327999 W
PLW13 0.21969999 W
F2 - Processing parameters
SI 32768
SF 125.7577684 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
32
Figure S29. 1H NMR Spectrum of 12d
33
Figure S30. 13
C NMR Spectrum of 12d 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.50
28
.73
29
.99
35
.03
37
.81
41
.78
53
.13
55
.39
76
.88
77
.20
77
.52
11
3.6
3
11
8.7
4
11
9.1
9
12
3.6
1
13
1.0
4
15
0.7
7
15
8.9
5
16
5.1
1
19
3.7
1
20
7.1
5
Current Data Parameters
NAME INN-MVD-89-13C
EXPNO 7
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121207
Time 0.43
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 104
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 294.8 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127552 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
34
Figure S31. 1H NMR Spectrum of 12e
10 9 8 7 6 5 4 3 2 1 0 ppm
0.4
2
27
.45
14
.08
9.6
8
9.8
9
10
.28
9.8
6
30
.45
9.7
2
4.5
2
1.0
0
Current Data Parameters
NAME INN-MVD-93-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121117
Time 16.46
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 9
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 32
DW 60.800 usec
DE 6.50 usec
TE 292.8 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
35
Figure S32. 13
C NMR Spectrum of 12e
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.61
28
.72
30
.01
35
.00
37
.80
41
.65
53
.19
55
.98
56
.08
76
.88
77
.20
77
.52
11
0.8
3
11
3.6
9
11
8.6
7
11
9.3
6
12
2.0
8
12
3.9
0
14
8.4
3
15
0.8
7
16
5.1
8
19
3.7
4
20
7.1
1Current Data Parameters
NAME INN-MVD-93-13C
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121117
Time 16.48
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 156
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 293.1 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127560 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
36
Figure S33. 1H NMR Spectrum of 12f
10 9 8 7 6 5 4 3 2 1 0 ppm
40
.10
19
.51
12
.81
12
.49
13
.53
13
.45
12
.68
12
.16
6.4
7
1.0
0
Current Data Parameters
NAME INN-MVD-189-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140217
Time 21.55
INSTRUM spect
PROBHD 5 mm SEI 1H/D-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 57
DW 60.800 usec
DE 6.50 usec
TE 293.4 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 6.75 usec
PL1 -3.00 dB
PL1W 16.73965454 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300103 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
37
Figure S34. 13
C NMR Spectrum of 12f
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.45
28
.69
29
.96
35
.01
37
.75
41
.69
53
.06
76
.88
77
.20
77
.51
10
1.1
3
10
8.0
7
11
0.6
0
11
8.7
0
11
9.2
7
12
3.2
8
12
5.0
0
14
7.0
0
14
7.3
7
15
1.0
3
16
5.0
8
19
3.6
2
20
7.0
6Current Data Parameters
NAME INN-MVD-189-13C
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140217
Time 21.59
INSTRUM spect
PROBHD 5 mm SEI 1H/D-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 580
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 32
DW 20.800 usec
DE 6.50 usec
TE 294.3 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127573 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
38
Figure S35. 1H NMR Spectrum of 12g
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
7
1.5
8
0.7
3
0.5
6
0.4
6
0.5
7
0.5
7
0.0
9
1.0
0
Current Data Parameters
NAME INN-MVD-90-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121117
Time 16.58
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 12
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 32
DW 60.800 usec
DE 6.50 usec
TE 292.9 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
39
Figure S36. 13
C NMR Spectrum of 12g
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.40
28
.72
30
.02
35
.09
37
.75
41
.54
53
.05
76
.88
77
.20
77
.52
11
8.5
2
11
8.5
9
12
8.3
4
12
9.8
9
13
1.2
5
13
3.3
5
15
1.3
7
16
5.4
0
19
3.7
0
20
6.9
0Current Data Parameters
NAME INN-MVD-90-13C
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121117
Time 17.01
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 285
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 293.4 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127542 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
40
Figure S37. 1H NMR Spectrum of 12h
10 9 8 7 6 5 4 3 2 1 0 ppm
2.7
8
1.3
8
0.9
5
0.9
0
0.9
5
0.9
3
1.1
5
1.0
0
Current Data Parameters
NAME INN-MVD-198-1H
EXPNO 8
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140228
Time 23.29
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 7
DS 2
SWH 10000.000 Hz
FIDRES 0.152588 Hz
AQ 3.2767999 sec
RG 30.72
DW 50.000 usec
DE 6.50 usec
TE 294.7 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 500.1330885 MHz
NUC1 1H
P1 13.00 usec
PLW1 13.00000000 W
F2 - Processing parameters
SI 65536
SF 500.1300020 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
41
Figure S38. 13
C NMR Spectrum of 12h
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.42
28
.73
30
.03
35
.09
37
.77
41
.54
53
.06
76
.95
77
.20
77
.46
11
8.4
9
11
8.6
4
12
1.6
0
13
0.3
9
13
1.3
0
13
1.5
9
15
1.3
6
16
5.4
1
19
3.6
7
20
6.8
7Current Data Parameters
NAME INN-MVD-198-13C
EXPNO 9
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140228
Time 23.29
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 80
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010048 sec
RG 197.27
DW 16.800 usec
DE 6.50 usec
TE 294.8 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 125.7703637 MHz
NUC1 13C
P1 8.90 usec
PLW1 103.00000000 W
======== CHANNEL f2 ========
SFO2 500.1320005 MHz
NUC2 1H
CPDPRG[2 waltz16
PCPD2 80.00 usec
PLW2 13.00000000 W
PLW12 0.34327999 W
PLW13 0.21969999 W
F2 - Processing parameters
SI 32768
SF 125.7577692 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
42
Figure S39. 1H NMR Spectrum of 12i
10 9 8 7 6 5 4 3 2 1 0 ppm
0.5
6
5.9
4
2.7
6
2.0
2
1.9
2
2.0
6
1.9
6
1.0
1
0.5
7
0.8
9
1.0
0
Current Data Parameters
NAME INN-MVD-91-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121116
Time 1.17
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 10
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 144
DW 60.800 usec
DE 6.50 usec
TE 293.6 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
43
Figure S40. 13
C NMR Spectrum of 12i
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
21
.17
28
.70
30
.03
34
.93
37
.79
41
.71
53
.22
76
.88
77
.19
77
.51
11
3.1
3
11
8.6
3
12
5.4
3
12
7.2
2
12
8.5
9
13
1.9
1
15
1.9
2
16
5.2
8
19
3.4
4
20
6.9
5Current Data Parameters
NAME INN-MVD-91-13C
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121116
Time 1.20
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 209
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 294.1 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127530 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
44
Figure S41. 1H NMR Spectrum of 12j
10 9 8 7 6 5 4 3 2 1 0 ppm
3.0
3
1.3
7
1.0
0
0.9
3
1.0
8
0.9
4
0.0
3
0.9
3
1.0
4
0.5
7
1.0
0
Current Data Parameters
NAME INN-MVD-193-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140220
Time 1.55
INSTRUM spect
PROBHD 5 mm SEI 1H/D-
PULPROG zg30
TD 52816
SOLVENT CDCl3
NS 19
DS 0
SWH 8802.817 Hz
FIDRES 0.166670 Hz
AQ 2.9999487 sec
RG 40.3
DW 56.800 usec
DE 6.50 usec
TE 295.3 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 6.75 usec
PL1 -3.00 dB
PL1W 16.73965454 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300103 MHz
WDW EM
SSB 0
LB 0 Hz
GB 0
PC 1.00
45
Figure S42. 13
C NMR Spectrum of 12j
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.60
28
.79
28
.81
29
.77
35
.15
37
.78
41
.56
52
.73
76
.88
77
.20
77
.52
11
7.0
5
12
0.4
3
12
5.3
3
12
5.7
3
12
5.8
0
12
6.0
2
12
7.9
2
12
8.3
3
12
8.4
1
12
9.5
0
13
2.6
6
13
3.6
5
15
2.1
5
16
4.8
7
19
2.9
6
20
6.9
3Current Data Parameters
NAME INN-MVD-193-13C
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140220
Time 2.05
INSTRUM spect
PROBHD 5 mm SEI 1H/D-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 183
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 181
DW 20.800 usec
DE 6.50 usec
TE 295.7 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 13.00 usec
PL1 -3.00 dB
PL1W 71.16858673 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 18.48 dB
PL13 19.00 dB
PL2W 16.73965454 W
PL12W 0.11905469 W
PL13W 0.10562007 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127608 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
46
Figure S43. 1H NMR Spectrum of 13a
47
Figure S44. 13
C NMR Spectrum of13a
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.38
22
.56
23
.81
29
.92
38
.71
41
.72
76
.94
77
.20
77
.45
11
9.7
2
11
9.9
0
12
7.4
0
12
8.0
5
12
9.8
8
13
1.4
5
15
0.8
5
16
6.0
5
19
4.1
2
20
7.0
4Current Data Parameters
NAME INN-MVD-211-13C
EXPNO 10
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140310
Time 22.13
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 54
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010048 sec
RG 197.27
DW 16.800 usec
DE 6.50 usec
TE 297.1 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 125.7703637 MHz
NUC1 13C
P1 8.90 usec
PLW1 103.00000000 W
======== CHANNEL f2 ========
SFO2 500.1320005 MHz
NUC2 1H
CPDPRG[2 waltz16
PCPD2 80.00 usec
PLW2 13.00000000 W
PLW12 0.34327999 W
PLW13 0.21969999 W
F2 - Processing parameters
SI 32768
SF 125.7577755 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
48
Figure S45. 1H NMR Spectrum of 13b
10 9 8 7 6 5 4 3 2 1 0 ppm
0.0
4
0.6
4
0.5
9
0.7
1
0.5
7
0.5
0
0.4
6
0.5
2
0.4
4
0.5
6
Current Data Parameters
NAME INN-MVD-82-1H
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121116
Time 0.47
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 80.6
DW 60.800 usec
DE 6.50 usec
TE 293.8 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
49
Figure S46. 13
C NMR Spectrum of 13b
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.41
21
.41
22
.59
23
.84
29
.95
38
.75
41
.79
76
.88
77
.20
77
.52
11
9.6
4
11
9.9
7
12
8.4
0
12
8.8
5
12
9.7
3
13
7.0
9
15
0.6
5
16
5.9
8
19
4.1
3
20
7.1
2Current Data Parameters
NAME INN-MVD-82-13C
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121116
Time 0.50
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 100
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 294.3 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127564 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
50
Figure S47. 1H NMR Spectrum of 13c
10 9 8 7 6 5 4 3 2 1 0 ppm
2.2
2
1.8
4
1.5
7
1.6
0
1.5
7
1.6
1
2.6
0
0.8
1
1.6
2
1.0
0
Current Data Parameters
NAME INN-MVD-208-1H
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140310
Time 21.43
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 2
SWH 10000.000 Hz
FIDRES 0.152588 Hz
AQ 3.2767999 sec
RG 30.72
DW 50.000 usec
DE 6.50 usec
TE 296.8 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 500.1330885 MHz
NUC1 1H
P1 13.00 usec
PLW1 13.00000000 W
F2 - Processing parameters
SI 65536
SF 500.1300111 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
51
Figure S48. 13
C NMR Spectrum of 13c
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.50
22
.57
23
.85
29
.95
38
.77
41
.71
55
.38
76
.95
77
.20
77
.45
11
3.2
6
11
5.6
0
11
9.6
3
11
9.9
3
12
2.3
0
12
9.0
2
13
2.7
8
15
0.9
8
15
9.2
6
16
6.0
3
19
4.0
1
20
7.0
2
Current Data Parameters
NAME INN-MVD-208-13C
EXPNO 6
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140310
Time 21.49
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 141
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010048 sec
RG 197.27
DW 16.800 usec
DE 6.50 usec
TE 297.4 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 125.7703637 MHz
NUC1 13C
P1 8.90 usec
PLW1 103.00000000 W
======== CHANNEL f2 ========
SFO2 500.1320005 MHz
NUC2 1H
CPDPRG[2 waltz16
PCPD2 80.00 usec
PLW2 13.00000000 W
PLW12 0.34327999 W
PLW13 0.21969999 W
F2 - Processing parameters
SI 32768
SF 125.7577719 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
52
Figure S49. 1H NMR Spectrum of 13d
10 9 8 7 6 5 4 3 2 1 0 ppm
0.2
0
4.9
6
2.0
9
2.1
6
4.1
5
3.0
0
1.9
3
2.3
4
Current Data Parameters
NAME INN-MVD-99-1H
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121130
Time 1.10
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 9
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 32
DW 60.800 usec
DE 6.50 usec
TE 293.7 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
53
Figure S50. 13
C NMR Spectrum of 13d
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.40
22
.60
23
.85
29
.97
38
.76
41
.76
55
.37
76
.88
77
.20
77
.52
11
3.6
0
11
9.3
1
11
9.9
6
12
3.6
7
13
1.0
2
15
0.4
7
15
8.9
4
16
5.9
7
19
4.2
5
20
7.1
4Current Data Parameters
NAME INN-MVD-99-13C
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121130
Time 1.11
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 100
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 293.7 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127563 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
54
Figure S49. 1H NMR Spectrum of 13d
55
Figure S52. 13
C NMR Spectrum of 13e
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.53
22
.58
23
.88
30
.01
38
.83
41
.66
55
.98
56
.07
76
.88
77
.20
77
.52
11
0.8
0
11
3.7
1
11
9.5
0
11
9.9
1
12
2.0
3
12
3.9
7
14
8.4
3
15
0.5
9
16
6.0
5
19
4.2
8
20
7.1
1Current Data Parameters
NAME INN-MVD-100-C13
EXPNO 23
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121211
Time 17.23
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 169
DS 2
SWH 27777.777 Hz
FIDRES 0.423855 Hz
AQ 1.1796480 sec
RG 912
DW 18.000 usec
DE 6.50 usec
TE 293.1 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6242389 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127550 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
56
Figure S49. 1H NMR Spectrum of 13d
57
Figure S54. 13
C NMR Spectrum of 13f
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.17
22
.42
23
.66
29
.85
38
.54
41
.36
11
8.6
0
11
9.5
6
12
1.4
5
13
0.3
4
13
1.1
2
13
1.4
4
15
0.8
8
16
6.1
0
19
4.0
3
20
6.7
0
Current Data Parameters
NAME INN-MVD-209-13C
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140307
Time 23.31
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 281
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010048 sec
RG 197.27
DW 16.800 usec
DE 6.50 usec
TE 295.8 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 125.7703637 MHz
NUC1 13C
P1 8.90 usec
PLW1 103.00000000 W
======== CHANNEL f2 ========
SFO2 500.1320005 MHz
NUC2 1H
CPDPRG[2 waltz16
PCPD2 80.00 usec
PLW2 13.00000000 W
PLW12 0.34327999 W
PLW13 0.21969999 W
F2 - Processing parameters
SI 32768
SF 125.7577890 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
58
Figure S55. 1H NMR Spectrum of 13g
10 9 8 7 6 5 4 3 2 1 0 ppm
0.1
2
2.8
8
1.1
2
2.2
3
1.0
8
0.5
8
0.1
8
1.0
0
Current Data Parameters
NAME INN-MVD-101-1H
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121130
Time 0.58
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 12
DS 0
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 32
DW 60.800 usec
DE 6.50 usec
TE 293.7 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 13.50 usec
PL1 -1.00 dB
PL1W 10.56200695 W
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300095 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
59
Figure S56. 13
C NMR Spectrum of 13g
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.99
22
.44
23
.83
30
.00
38
.81
41
.69
76
.88
77
.20
77
.52
11
3.1
4
11
9.8
1
12
5.5
0
12
7.1
6
12
8.5
2
13
1.8
9
15
1.6
8
16
6.1
3
19
3.9
7
20
6.9
5Current Data Parameters
NAME INN-MVD-101-13C
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20121130
Time 1.00
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 100
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 2050
DW 20.800 usec
DE 6.50 usec
TE 293.9 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 8.75 usec
PL1 -2.00 dB
PL1W 56.53121948 W
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -1.00 dB
PL12 14.50 dB
PL13 14.50 dB
PL2W 10.56200695 W
PL12W 0.29767781 W
PL13W 0.29767781 W
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127557 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
60
Figure S57. 1H NMR Spectrum of 13h
10 9 8 7 6 5 4 3 2 1 0 ppm
3.0
0
2.0
7
2.1
6
1.9
9
2.0
1
2.1
4
0.1
1
1.0
4
1.0
7
2.1
0
1.0
5
2.0
4
Current Data Parameters
NAME INN-MVD--210-1H
EXPNO 5
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150218
Time 22.59
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16
DS 2
SWH 10000.000 Hz
FIDRES 0.152588 Hz
AQ 3.2767999 sec
RG 30.72
DW 50.000 usec
DE 6.50 usec
TE 299.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 500.1330885 MHz
NUC1 1H
P1 13.00 usec
PLW1 13.00000000 W
F2 - Processing parameters
SI 65536
SF 500.1300118 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
61
Figure S58. 13
C NMR Spectrum of 13h
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20
.59
22
.72
23
.88
29
.81
38
.45
41
.62
76
.95
77
.20
77
.45
11
7.2
8
12
1.6
8
12
5.3
7
12
5.8
3
12
5.8
4
12
6.0
6
12
7.9
2
12
8.4
0
12
8.4
7
12
9.6
3
13
2.7
4
13
3.6
9
15
1.8
7
16
5.8
2
19
3.6
7
20
6.9
9Current Data Parameters
NAME INN-MVD-210-13C
EXPNO 4
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140310
Time 21.36
INSTRUM spect
PROBHD 5 mm PABBO BB/
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 141
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010048 sec
RG 197.27
DW 16.800 usec
DE 6.50 usec
TE 297.2 K
D1 1.00000000 sec
D11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
SFO1 125.7703637 MHz
NUC1 13C
P1 8.90 usec
PLW1 103.00000000 W
======== CHANNEL f2 ========
SFO2 500.1320005 MHz
NUC2 1H
CPDPRG[2 waltz16
PCPD2 80.00 usec
PLW2 13.00000000 W
PLW12 0.34327999 W
PLW13 0.21969999 W
F2 - Processing parameters
SI 32768
SF 125.7577700 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40