N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
195 195
a
b
b
c
e
e
d
d
a
c
a
a
a
a
a
a
a
b
b
b
b
b
b
b
c
c
c
c
c
e
c
d
d
c
d
d
d
d
Solvent:
CDCl 3 DMSO
a 8.59
8.58
b 7.25
7.38
c 7.62
7.75
Solvent:
CDCl 3
* DMSO **
a 9.00
8.98
b 7.97
8.14
c 8.43
8.67
8.19
8.84
9.48
9.88
9.22
8.26
7.83
8.78
8.63
8.43
9.27
8.98
8.44
8.11
7.40
9.23
7.56
7.22
8.54
7.38
7.34
8.24
7.32
* p-toluylsulfonate
** HSO 3
–
(in acetone)
3 J ab 6.5
4 J ac 1.1
5 J ad 0.6
4 J ae 1.9
3 J bc 7.7
4 J bd 2.1
3 J ab 2.7
4 J ac 0.0
5 J bc 2.2
3 J ab 4.9
4 J ac 2.0
5 J ad 3.5
3 J bc 8.4
3 J ab 5.3
4 J ac 1.0
5 J ad 1.0
3 J bc 8.0
4 J bd 2.5
3 J cd 6.5
3 J ab 5.0
4 J ac 2.5
4 J ad 0
5 J bd 1.5
3 J ab 4.1
5 J ac 0.8
4 J ad 0.6
4 J bc 0.4
3 J ab 6.8
4 J ac 1.6
4 J ad 2.0
3 J bc 4.9
5 J bd 1.0
4 J cd 0
3 J ab 6.0
4 J ac 1.9
5 J ad 0.9
4 J ae 0.4
3 J bc 7.6
4 J bd 1.6
3 J ab 6.0
4 J ac 1.6
5 J ad 0.8
4 J ae 1.0
3 J bc 7.9
4 J bd 1.4
N
N
H
+
N
O
N
N
N
N
N
N
N
N
O
N
N
N
N
O
N N
N N
O
N
N
5.6 Heteroaromatic Compounds