N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
185
5.4 Alicyclics
185
1 H Chemical Shifts and Coupling Constants of Monosubstituted Cyclopropanes (δ in ppm, J in Hz)
Substituent R
H a H b;d H c;e
3 J ab
3 J ac
2 J bc
3 J bd
3 J be
3 J ce
–H
0.20 0.20 0.20 9.0 5.6 -4.3 9.0 5.6 9.0
–CH 3
1.00 0.35 0.15
–CH 2 OH
1.14 0.40 0.30
–CH=CH 2
1.35 0.64 0.34 8.2 4.9 -4.5 9.3 6.2 9.0
–phenyl
1.83 0.89 0.65 9.5 6.3 -4.5 9.5 5.2 8.9
–F
4.32 0.69 0.27 5.9 2.4 -6.7 10.8 7.7 12.0
–Cl
2.55 0.87 0.74 7.0 3.6 -6.0 10.3 7.1 10.6
–Br
2.83 0.96 0.81 7.1 3.8 -6.1 10.2 7.0 10.5
–I
2.31 1.04 0.76 7.5 4.4 -5.9 9.9 6.6 10.0
–OH
3.35 0.40 0.48 6.2 2.9 -5.4 10.3 6.8 10.9
–NH 2
2.23 0.32 0.20 6.6 3.6 -4.3 9.7 6.2 9.9
–NH 3
+
1.06 0.52 0.34
–NO 2
4.21 1.13 1.60 7.0 3.4 -5.5 10.1 8.3 11.3
–C– – – N
1.29 0.96 1.04 8.4 5.1 -4.7 9.2 7.1 9.5
–CHO
1.79 0.99 1.03 8.0 4.6 -4.5 8.8 7.0 9.6
–COCH 3
1.83 0.77 0.93 7.9 4.6 -3.5 9.2 7.0 9.5
–CO–cyclopropyl 1.70 0.56 1.02 7.9 4.6 -3.5 9.1 7.0 9.5
–CO–phenyl
2.65 1.01 1.23
–COOH
1.59 0.91 1.05 8.0 4.6 -4.0 9.3 7.1 9.7
–COOCH 3
1.61 0.86 0.98 8.0 4.6 -3.4 8.8 6.9 9.6
–CONH 2
1.39 0.70 0.95
–COF
1.66 1.11 1.20 8.0 4.6 -4.5 10.1 7.5 9.3
–COCl
2.11 1.18 1.28 7.9 4.4 -4.5 9.2 7.6 10.0
–Li
-2.53 0.43 -0.12 10.3 9.1 -1.6 7.7 3.2 6.5
–MgBr
-2.04 0.25 -0.13 11.0 8.5 -1.7 7.8 3.5 6.6
–B(cyclopropyl) 2 -0.25 0.61 0.66 8.9 5.8 -3.3 8.2 5.9 8.4
–Si(cyclopropyl) 3 -0.67 0.49 0.36 9.7 6.9 -3.4 8.4 5.1 8.1
–P + (phenyl) 3
3.28 1.82 0.63
–Hg–cyclopropyl 0.00 0.75 0.47 9.6 6.9 -3.7 8.5 4.8 7.9
a
R
H
H
H
H
H
d
c
b
e
C
X
O
N
O
||
C
M
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
185
5.4 Alicyclics
185
1 H Chemical Shifts and Coupling Constants of Monosubstituted Cyclopropanes (δ in ppm, J in Hz)
Substituent R
H a H b;d H c;e
3 J ab
3 J ac
2 J bc
3 J bd
3 J be
3 J ce
–H
0.20 0.20 0.20 9.0 5.6 -4.3 9.0 5.6 9.0
–CH 3
1.00 0.35 0.15
–CH 2 OH
1.14 0.40 0.30
–CH=CH 2
1.35 0.64 0.34 8.2 4.9 -4.5 9.3 6.2 9.0
–phenyl
1.83 0.89 0.65 9.5 6.3 -4.5 9.5 5.2 8.9
–F
4.32 0.69 0.27 5.9 2.4 -6.7 10.8 7.7 12.0
–Cl
2.55 0.87 0.74 7.0 3.6 -6.0 10.3 7.1 10.6
–Br
2.83 0.96 0.81 7.1 3.8 -6.1 10.2 7.0 10.5
–I
2.31 1.04 0.76 7.5 4.4 -5.9 9.9 6.6 10.0
–OH
3.35 0.40 0.48 6.2 2.9 -5.4 10.3 6.8 10.9
–NH 2
2.23 0.32 0.20 6.6 3.6 -4.3 9.7 6.2 9.9
–NH 3
+
1.06 0.52 0.34
–NO 2
4.21 1.13 1.60 7.0 3.4 -5.5 10.1 8.3 11.3
–C– – – N
1.29 0.96 1.04 8.4 5.1 -4.7 9.2 7.1 9.5
–CHO
1.79 0.99 1.03 8.0 4.6 -4.5 8.8 7.0 9.6
–COCH 3
1.83 0.77 0.93 7.9 4.6 -3.5 9.2 7.0 9.5
–CO–cyclopropyl 1.70 0.56 1.02 7.9 4.6 -3.5 9.1 7.0 9.5
–CO–phenyl
2.65 1.01 1.23
–COOH
1.59 0.91 1.05 8.0 4.6 -4.0 9.3 7.1 9.7
–COOCH 3
1.61 0.86 0.98 8.0 4.6 -3.4 8.8 6.9 9.6
–CONH 2
1.39 0.70 0.95
–COF
1.66 1.11 1.20 8.0 4.6 -4.5 10.1 7.5 9.3
–COCl
2.11 1.18 1.28 7.9 4.4 -4.5 9.2 7.6 10.0
–Li
-2.53 0.43 -0.12 10.3 9.1 -1.6 7.7 3.2 6.5
–MgBr
-2.04 0.25 -0.13 11.0 8.5 -1.7 7.8 3.5 6.6
–B(cyclopropyl) 2 -0.25 0.61 0.66 8.9 5.8 -3.3 8.2 5.9 8.4
–Si(cyclopropyl) 3 -0.67 0.49 0.36 9.7 6.9 -3.4 8.4 5.1 8.1
–P + (phenyl) 3
3.28 1.82 0.63
–Hg–cyclopropyl 0.00 0.75 0.47 9.6 6.9 -3.7 8.5 4.8 7.9
a
R
H
H
H
H
H
d
c
b
e
C
X
O
N
O
||
C
M