Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a...
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S1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra Brun, a Lídia Garcia, a Iván González, a Anna Torrent, a Anna Dachs, a Anna Pla- Quintana, a Teodor Parella, b Anna Roglans.* , a a Department of Chemistry, Universitat de Girona, Campus de Montilivi, s/n. E-17071-Girona, Spain. Fax: 0034 972 418150; Tel:0034 972 4182 75; E-mail: [email protected]. b Servei de RMN, Universitat Autònoma de Barcelona, Cerdanyola, E-08193-Barcelona, Spain. Tel-Fax: 0034 93 5812291; E-mail: [email protected]. Contents Original spectra for the products: 1 H- and 13 C NMR spectra of 2a: S2-S3 1 H- and 13 C NMR, COSY and HSQC spectra of 2b: S4-S7 1 H- and 13 C NMR, COSY, NOESY and HSQC spectra of 2c: S8-S12 1 H- and 13 C NMR, COSY, NOESY, HSQC and HMBC spectra of 2d:S13-S18 1 H- and 13 C NMR, COSY, NOESY, HSQC and HMBC spectra of 2f: S19-S24 1 H- and 13 C NMR, COSY, NOESY, HSQC and HMBC spectra of 2g:S25-S30 1 H- and 13 C NMR spectra of 2h: S31-S32 Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Transcript of Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a...
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S1
Electronic Supplementary Information
Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems
Sandra Brun,a Lídia Garcia,a Iván González,a Anna Torrent,a Anna Dachs,a Anna Pla-Quintana,a Teodor Parella,b Anna Roglans.*, a
a Department of Chemistry, Universitat de Girona, Campus de Montilivi, s/n. E-17071-Girona, Spain. Fax: 0034 972 418150; Tel:0034 972 4182 75; E-mail: [email protected]. b Servei de RMN, Universitat Autònoma de Barcelona, Cerdanyola, E-08193-Barcelona, Spain. Tel-Fax: 0034 93 5812291; E-mail: [email protected].
Contents
Original spectra for the products:
1H- and 13C NMR spectra of 2a: S2-S3
1H- and 13C NMR, COSY and HSQC spectra of 2b: S4-S7
1H- and 13C NMR, COSY, NOESY and HSQC spectra of 2c: S8-S12
1H- and 13C NMR, COSY, NOESY, HSQC and HMBC spectra of 2d:S13-S18
1H- and 13C NMR, COSY, NOESY, HSQC and HMBC spectra of 2f: S19-S24
1H- and 13C NMR, COSY, NOESY, HSQC and HMBC spectra of 2g:S25-S30
1H- and 13C NMR spectra of 2h: S31-S32
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S2
NSO2Ar
SO2Ar
NArO2S
N2a
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S3
NSO2Ar
SO2Ar
NArO2S
N2a
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S4
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.
90
01
.2
66
1.
27
51
.2
80
1.
29
51
.4
78
1.
48
61
.5
02
1.
51
01
.6
40
1.
86
01
.8
65
1.
87
11
.8
97
1.
93
62
.0
67
2.
24
02
.2
60
2.
26
42
.2
85
2.
44
82
.4
57
2.
57
42
.5
91
2.
61
12
.7
86
2.
81
43
.6
31
3.
66
53
.6
94
3.
79
33
.8
21
3.
82
53
.8
55
3.
87
03
.8
86
3.
90
43
.9
32
3.
98
24
.0
08
4.
02
14
.1
35
4.
14
94
.1
63
4.
18
07
.2
87
7.
33
97
.3
46
7.
35
37
.3
62
7.
36
87
.6
43
7.
66
07
.6
82
7.
69
87
.7
14
7.
73
0
6.
96
52
.7
21
4.
20
5
2.
04
51
8.
39
64
.2
39
2.
00
0
3.
95
5
12
.1
02
3.
00
2
12
.0
30
12
.0
55
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
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S5
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
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S6
COSY
ppm
2345678 ppm
2
3
4
5
6
7
8
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
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S7
HSQC
ppm
2345678 ppm
20
40
60
80
100
120
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
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S8
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.
89
30
.9
04
0.
94
41
.2
00
1.
22
61
.2
80
1.
60
12
.0
75
2.
12
32
.2
83
2.
35
02
.3
73
2.
39
62
.4
29
2.
44
42
.4
64
2.
48
52
.5
18
2.
65
82
.6
79
2.
69
92
.8
22
2.
84
53
.0
94
3.
48
83
.5
19
3.
65
23
.6
68
3.
68
43
.7
15
3.
73
73
.8
58
3.
91
43
.9
43
3.
98
04
.0
12
4.
06
74
.0
91
4.
12
84
.1
57
4.
43
34
.4
52
5.
32
5
7.
31
07
.3
45
7.
36
07
.3
81
7.
39
67
.6
24
7.
63
77
.7
01
7.
71
77
.7
71
9.
42
0
25
.6
24
1.
95
51
.7
75
1.
80
7
2.
00
04
.1
04
3.
17
23
.7
88
3.
80
7
24
.4
96
4.
15
97
.1
35
NSO2Ar
SO2Ar
NArO2S
N
HH
2c
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S9
20406080100120140160 ppm
21
.5
90
22
.6
82
27
.8
44
29
.3
51
29
.6
46
29
.6
86
31
.9
13
37
.1
24
40
.2
82
46
.4
59
48
.6
82
48
.8
87
49
.6
06
49
.7
71
12
3.
57
91
23
.7
25
12
5.
23
71
27
.6
32
12
7.
69
61
27
.7
51
12
9.
11
31
29
.7
74
12
9.
90
11
32
.4
05
13
2.
76
61
32
.8
44
14
3.
84
41
43
.8
93
14
4.
12
4
NSO2Ar
SO2Ar
NArO2S
N
HH
2c
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S10
COSY
ppm
1234567 ppm
1
2
3
4
5
6
7
NSO2Ar
SO2Ar
NArO2S
N
HH
2c
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S11
NOESY
ppm
1234567 ppm
1
2
3
4
5
6
7
NSO2Ar
SO2Ar
NArO2S
N
HH
2c
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S12
HSQC
ppm
12345678 ppm
20
40
60
80
100
120
NSO2Ar
SO2Ar
NArO2S
N
HH
2c
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S13
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
9 8 7 6 5 4 3 2 1 0 ppm
1.
25
91
.2
70
1.
28
31
.3
87
1.
40
11
.4
07
1.
42
11
.4
41
1.
61
81
.8
41
1.
86
61
.8
88
2.
05
62
.2
80
2.
30
02
.3
18
2.
45
62
.4
66
2.
76
42
.7
87
3.
82
93
.8
48
3.
87
13
.9
95
4.
01
74
.0
93
4.
11
65
.3
12
7.
27
77
.3
38
7.
35
27
.3
70
7.
38
37
.6
37
7.
65
17
.6
61
7.
73
97
.7
49
7.
76
3
1.
03
1.
82
0.
97
4.
55
0.
89
1.
88
1.
01
0.
95
2.
98
1.
96
1.
00
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S14
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
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S15
ppm
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2
3
4
5
6
7
COSY
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S16
ppm
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
2
3
4
5
6
7
NOESY
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S17
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
HSQC
ppm
2.02.53.03.54.04.55.05.56.06.57.07.5 ppm
20
40
60
80
100
120
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S18
ppm
2.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
140
120
100
80
60
40
20
HMBC
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S19
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
10 9 8 7 6 5 4 3 2 1 ppm
2.
26
02
.2
63
2.
28
22
.4
00
2.
42
62
.4
65
3.
01
33
.0
33
3.
49
53
.5
09
3.
62
33
.6
25
3.
69
43
.7
86
3.
80
43
.8
11
3.
88
13
.9
14
4.
03
14
.0
60
4.
41
14
.4
30
6.
88
26
.8
96
7.
12
17
.1
35
7.
15
07
.1
59
7.
17
37
.1
90
7.
20
67
.2
42
7.
25
87
.2
87
7.
34
07
.3
56
7.
46
17
.4
77
7.
54
47
.5
61
7.
71
17
.7
28
1.
00
09
.2
74
1.
84
60
.9
09
1.
97
94
.7
49
1.
01
70
.9
32
1.
78
64
.8
33
1.
89
32
.0
32
1.
89
21
.8
71
2.
00
8
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S20
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
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S21
COSY
ppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
3
4
5
6
7
8
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S22
NOESY
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
ppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
3
4
5
6
7
8
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S23
HSQC
ppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
20
40
60
80
100
120
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S24
HMBC
ppm
2.53.03.54.04.55.05.56.06.57.07.58.0 ppm
20
40
60
80
100
120
140
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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S25
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2g
2.53.03.54.04.55.05.56.06.57.07.58.0 ppm
2.
41
62
.4
25
2.
43
42
.4
50
2.
46
12
.4
75
2.
48
32
.4
95
2.
69
92
.7
15
3.
60
93
.6
23
3.
64
13
.7
04
3.
72
63
.7
85
3.
85
93
.8
97
3.
91
24
.0
23
4.
07
14
.0
96
6.
96
06
.9
67
6.
97
36
.9
75
7.
16
47
.1
70
7.
17
37
.1
79
7.
19
37
.2
02
7.
21
67
.2
77
7.
34
37
.3
57
7.
45
67
.4
70
7.
64
27
.6
56
7.
67
97
.6
93
5.
63
0.
96
1.
39
2.
08
0.
52
1.
10
0.
99
3.
37
1.
14
0.
97
0.
96
1.
00
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 26: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/26.jpg)
S26
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2g
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 27: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/27.jpg)
S27
COSY
ppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
3
4
5
6
7
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2g
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 28: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/28.jpg)
S28
NOESY
ppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
3
4
5
6
7
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2g
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 29: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/29.jpg)
S29
HSQC
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2gppm
2.53.03.54.04.55.05.56.06.57.07.5 ppm
20
40
60
80
100
120
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 30: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/30.jpg)
S30
HMBC
ppm
2.53.03.54.04.55.05.56.06.57.07.58.0 ppm
20
40
60
80
100
120
140
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2g
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 31: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/31.jpg)
S31
N
N
N
SO2Ar
SO2Ar
ArO2S
2h
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
![Page 32: Electronic Supplementary InformationS1 Electronic Supplementary Information Fused Tetracycles with a Benzene or Cyclohexadiene Core: [2+2+2] Cycloadditions on Macrocyclic Systems Sandra](https://reader036.fdocuments.us/reader036/viewer/2022081623/61499a8712c9616cbc68de4f/html5/thumbnails/32.jpg)
S32
N
N
N
SO2Ar
SO2Ar
ArO2S
2h
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
