N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
186
5 1 H NMR
1 H Chemical Shifts of Equatorially and Axially Substituted Cyclohexanes (δ
in ppm, J in Hz)
Eq. substituent R H 1,ax H 2,ax H 2,eq H 3,ax H 3,eq H 4,ax H 4,eq
–D*
1.12
1.12
1.60
1.12
1.60
1.12
1.60
–C*
1.27
0.81
1.57
1.15
1.60
1.06
1.58
–C– – – C*
2.25
1.36
1.98
1.20
1.73
1.17
1.67
–phenyl*
2.46
–F*
4.49
1.42
2.15
1.28
1.86
1.12
1.65
–Cl*
3.88
1.58
2.22
1.33
1.84
1.18
1.68
–Br*
4.09
1.75
2.33
1.35
1.80
1.22
1.72
–I*
4.18
1.97
2.45
1.36
1.67
1.30
1.80
–OH**
3.52
1.22
2.01
1.05
1.78
0.97
–OCOCH 3 *
4.74
1.72
1.85
1.35
1.41
1.25
1.55
–NH 2 **
2.55
1.03
1.89
1.03
1.76
0.96
–NHCOCH 3 **
3.67
1.07
2.01
1.11
1.78
1.01
–NO 2 *
4.38
2.23
1.85
1.38
1.85
1.28
1.67
–C– – – N**
2.31
1.53
2.16
0.98
1.86
1.03
–SH*
2.79
1.34
2.01
1.31
1.75
1.22
1.61
–COOCH 3 *
2.30
1.44
1.90
1.27
1.75
1.24
1.64
Ax. substituent R H 1,eq H 2,ax H 2,eq H 3,ax H 3,eq H 4,ax H 4,eq
–D*
1.60
1.12
1.60
1.12
1.60
1.12
1.60
–C*
1.93
1.37
1.40
1.39
1.34
1.06
1.58
–C– – – C*
2.87
1.48
1.78
–phenyl*
3.16
2.42
–F*
4.94
1.43
2.03
1.63
1.75
1.28
1.58
–Cl*
4.59
1.76
2.00
1.77
1.75
1.26
1.75
–Br*
4.80
1.81
2.08
1.79
1.60
1.24
1.78
–I*
4.96
1.53
2.06
1.72
1.62
1.26
1.73
–OH**
4.03
1.49
1.83
1.35
1.54
0.99
–OCOCH 3 *
5.31
1.49
2.51
–NH 2 **
3.15
1.54
1.65
1.27
1.53
0.96
–NHCOCH 3 **
4.11
1.51
1.85
1.03
1.66
1.04
–NO 2 **
4.43
1.6
2.6
–C– – – N**
2.96
1.54
2.00
1.50
1.70
1.20
–SH**
3.43
1.5
1.9
R
H
H
H
H
H
H
R'
1
4
3
2
H
H
H
H
H
H
R'
R
1
4
3
2
C
X
O
N
S
* R': –H; ** R': –tert-butyl
C
X
O
N
S