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
S2
NSO2Ar
SO2Ar
NArO2S
N2a
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
S3
NSO2Ar
SO2Ar
NArO2S
N2a
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
S5
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
S6
COSY
ppm
2345678 ppm
2
3
4
5
6
7
8
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
S7
HSQC
ppm
2345678 ppm
20
40
60
80
100
120
NSO2Ar
SO2Ar
NArO2S
N
HH
2b
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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
S10
COSY
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
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
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
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
S14
SO2Ar
NArO2S
N
HH
NSO2Ar
2d
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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
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
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
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
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
S20
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2f
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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
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
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
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
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
S26
N
N
N
SO2Ar
SO2Ar
ArO2SPhH
2g
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
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
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
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
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
S31
N
N
N
SO2Ar
SO2Ar
ArO2S
2h
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008
S32
N
N
N
SO2Ar
SO2Ar
ArO2S
2h
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2008