European Journal of Organic Chemistry
10.1002/ejoc.202000068
FULL PAPER
4
-(tert-Butyl)-4'-methyl-1,1'-biphenyl (Table 2, entry 3)[30]
R
7
f
=0.65 (EA/hexane 1:9); 1H NMR (400 MHz, CDCl
.06 (d, J= 8.8 Hz, 2H), 7.59 (d, J= 8.8 Hz, 2H), 7.71 (dd, J=14.2 Hz,
J=8.6 Hz,2H); 13C NMR (100 MHz, CDCl
) δ 55.2, 114.3, 125.5, 125.6,
3
) δ 3.91 (s, 3H),
1
3
R
f
= 0.5 (hexane); H NMR (400 MHz, CDCl
3
) δ 1.59 (s, 9H), 2.60 (s, 3H),
.44 (dd, J= 8.4 Hz, J=0.8Hz, 2H), 7.66-7.77 (m, 6H); 13C NMR (100 MHz,
CDCl ) δ 21.0, 31.3, 34.4, 125.6, 126.5, 126.8, 129.4, 136.5, 138.1,
38.2, 149.8.
125.6, 125.6, 126.7, 128.2, 132.0, 144.2, 159.8.
7
3
1
4'-Methoxy-[1,1'-biphenyl]-3-carbonitrile (Table 2, entry 12)[37]
Methyl 4'-methyl-[1,1'-biphenyl]-3-carboxylate (Table 2, entry 4)[31]
R
f
=0.6 (EA/hexane 1:5); H NMR (400 MHz, CDCl
1
3
) δ 3.88 (s, 3H), 7.00-
7
.04 (m, 2H), 7.50-7.58 (m, 3H), 7.60 (t, J= 1.4 Hz, 1H), 7.77-7.83 (m,
2H); 13C NMR (100 MHz, CDCl
) δ 55.2, 112.7, 114.4, 118.8, 128.0,
29.4, 129.9, 130.0, 130.8, 131.1, 141.8, 159.8.
= 0.55 (EA/hexane 1:9); 1H NMR (400 MHz, CDCl
.00 (s, 3H), 7.31 (d, J= 8 Hz, 2H), 7.51-7.59 (m, 3H), 7.80-7.82 (m, 1H),
.05-8.08 (m, 1H), 8,36 (t, J= 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl
) δ
0.9, 51.9, 126.7, 127.8, 127.8, 128.6, 129.4, 130.4, 131.1, 136.9, 137.3,
41.1, 166.8.
3
R
f
3
) δ 2.45 (s, 3H),
1
4
8
2
1
3
4-Methoxy-1,1'-biphenyl (Table 2, entry 13)[34]
R
f
= 0.65 (EA/hexane 1:5); 1H NMR (400 MHz, CDCl
7.11 (d, J= 8.8 Hz, 2H), 7.42-7.46 (m, 1H), 7.55 (dd, J= 8.2 Hz, J= 7.2 Hz,
H), 7.66-7.71 (m, 4H ); 13C NMR (100 MHz, CDCl
) δ 55.1, 114.1, 126.5,
126.6, 128.0, 128.6, 133.6, 140.7, 159.0.
3
) δ 3.94 (s, 3H),
Methyl 3'-methyl-[1,1'-biphenyl]-3-carboxylate (Table 2, entry 5)[32]
= 0.9 (EA/hexane 1:15); 1H NMR (400 MHz, CDCl
) δ 2.47 (s, 3H),
2
3
R
f
3
3
3
.99 (s, 3H), 7.23 (d, J= 7.2 Hz, 1H), 7.38 (t, J= 7.6 Hz, 1H), 7.46-7.53 (m,
H), 7.80 (d, J= 8 Hz, 1H), 8.08 (d, J= 7.6 Hz, 1H), 8.37 (s, 1H); 13C NMR
(2S,6'R)-2',4,6-Trimethoxy-6'-methyl-7-phenyl-3H-spiro[benzofuran-
(100 MHz, CDCl
3
) δ 21.1, 51.7, 123.9, 127.5, 127.9, 127.9, 128.2, 128.5,
2,1'-cyclohexan]-2'-ene-3,4'-dione (Scheme 1)
128.5, 130.3, 131.1, 138.1, 139.7,141.2, 166.6.
R
f
=0.16 (EA/hexane 1:1); m.p. = 119.2-122.5 °C. 1H NMR (500 MHz,
CDCl ) δ 0.96 (d, J=6.5 Hz, 3H), 2.34-2.39 (m, 1H), 2.68-2.74 (m, 1H),
3.03-3.09 (m, 1H), 3.61 (s, 3H), 3.91 (s, 3H), 4.01 (2, 3H), 5.50 (s, 1H),
(
6
4'-Methyl-[1,1'-biphenyl]-4-yl)(phenyl)methanone (Table 2, entry
)[33]
3
6
.17 (1H), 7.33-7.36 (m, 1H), 7.51-7.44 (m, 2H), 7.47 (d, J=7.0 Hz, 2H);
) δ 14.2, 36.2, 39.9, 56.0, 56.3, 56.4, 88.7,
9.6, 104.1, 104.4, 107.2, 127.2, 127.0, 130.5, 130.7, 158.5, 166.2,
1
3C NMR (125 MHz, CDCl
= 0.55 (EA/hexane 1:5); 1H NMR (400 MHz, CDCl
f 3
R ) δ 2.46 (s, 3H),
3
8
7
8
1
1
.33 (d, J= 7.6 Hz, 2H), 7.52-7.56 (m, 2H), 7.59-7.66 (m, 3H), 7.73 (d, J=
.8 Hz, 2H), 7.88-7.95 (m, 4H); 13C NMR (100 MHz, CDCl
171.6 (overlapped), 193.2, 197.3.
3
) δ 21.0, 21.0,
26.5, 126.9, 128.1, 129.5, 129.8, 130.6, 132.1, 135.7, 136.8, 137.6,
38.0, 145.0, 196.1.
2-Methyl-1,1'-biphenyl (Table 3, entry 1)[29]
Methyl [1,1'-biphenyl]-4-carboxylate (Table 2, entry 7)[19]
R
(
= 0.5 (hexane); 1H NMR (400 MHz, CDCl
m, 4H), 7.44-7.47 (m, 3H), 7.51-7.53 (m, 2H); 13C NMR (100 MHz,
CDCl 20.4, 125.7, 126.7, 127.2, 128.0, 129.1, 129.7,
30.2,135.2,141.9,141.9.
f
3
) δ 2.40 (s, 3H), 7.36-7.39
= 0.5 (EA/hexane 1:5); 1H NMR (400 MHz, CDCl
.41-7.48 (m, 1H), 7.49-7.51 (m, 2H), 7.64-7.69 (m, 4H), 8.15 (d, J= 8.4
Hz, 2H); 13C NMR (100 MHz, CDCl
) δ 51.8, 126.8, 127.0, 127.9, 128.7,
28.7, 129.9, 139.7, 145.3, 166.7.
3
)
δ
R
f
3
) δ 3.97 (s, 3H),
1
7
3
1
2,3'-Dimethyl-1,1'-biphenyl (Table 3, entry 2)[38]
1
[
1,1'-Biphenyl]-4-carbaldehyde (Table 2, entry 8)[34]
R
7
f
= 0.5 (hexane); H NMR (400 MHz, CDCl
3
) δ 2.48 (s, 3H), 2.60 (s, 3H),
) δ 20.4,
21.4, 125.6, 126.2, 127.1, 127.4, 127.8, 129.7, 129.8, 130.2, 135.2,
37.5, 141.9, 142.0.
.32-7.35 (m, 3H), 7.43-7.51 (m, 5H); 13C NMR (100 MHz, CDCl
3
= 0.4 (EA/hexane 1:10); 1H NMR (400 MHz, CDCl
H), 7.65 (d, J= 7.2 Hz, 2H), 7.76(d, J= 8 Hz, 2H), 7.96 (d, J= 8.4 Hz, 2H),
R
f
3
) δ 7.44-7.52 (m,
1
3
1
1
0.07 (s, 1H); 13C NMR (100 MHz, CDCl
30.1, 135.0, 139.5, 146.9, 191.7.
3
) δ 127.2, 127.4, 128.3, 128.8,
4'-Butoxy-2,3-dimethyl-1,1'-biphenyl (Table 3, entry 3)[39]
4
-Methoxy-4'-nitro-1,1'-biphenyl (Table 2, entry 9)[35]
R
1
f
= 0.4 (hexane); 1H NMR (400 MHz, CDCl
.61-1.67 (m, 2H), 1.88-1.95 (m, 2H), 2.28 (s, 3H), 2.45 (s, 3H), 4.11 (t,
J= 6.4 Hz, 2H), 7.04-7.06 (m, 2H), 7.18-7.25 (m, 3H), 7.33 (d, J= 8.8 Hz,
H); 13C NMR (100 MHz, CDCl
) δ 13.8, 16.9, 19.2, 20.6, 31.3, 67.6,
113.9, 125.1, 127.7, 128.5, 130.3, 134.1, 134.7, 137.0, 141.9, 157.9.
3
) δ 1.12 (t, J= 7.4 Hz, 3H),
1
R
f
= 0.3 (EA/hexane 1:9); H NMR (400 MHz, CDCl
3
) δ 3.89 (s, 3H), 7.03
2
3
(
(
d, J= 8.4 Hz, 2H), 7.58 (d, J= 8.4 Hz, 2H), 7.68 (d, J= 8.4 Hz, 2H), 8.25
d, J= 8.8 Hz, 2H); 13C NMR (100 MHz, CDCl
3
) δ 55.2, 114.4, 123.9,
126.8, 128.4, 130.8, 146.3, 147.0, 160.3.
2
,6-Dimethyl-1,1'-biphenyl (Table 3, entry 4)[40]
1
-(4'-Methyl-[1,1'-biphenyl]-4-yl)ethan-1-one (Table 2, entry 10)[29]
R
f
= 0.6 (hexane); 1H NMR (400 MHz, CDCl
(m, 5H), 7.57-7.61 (m, 1H), 7.67 (t, J= 7.2 Hz, 2H); 13C NMR (100 MHz,
CDCl ) δ 20.7, 126.5, 126.9 127.2, 128.3, 128.9, 135.9, 141.0,141.8.
3
) δ 2.32 (s, 6H), 7.37-7.45
1
R
f
= 0.5 (EA/hexane 1:5); H NMR (400 MHz, CDCl
3
) δ 2.44 (s, 3H), 2.63
3
(
2
1
s, 3H), 7.29 (d, J= 8 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.67 (d, J= 8.4 Hz,
H), 8.02 (d, J= 8.8 Hz, 2H); 13C NMR (100 MHz, CDCl
) δ 20.9, 26.3,
3
26.6, 126.8, 128.6, 129.4, 135.3, 136.6, 137.9, 145.3, 197.3.
4',6-Dimethoxy-[1,1'-biphenyl]-2-carbaldehyde (Table 3, entry 5)[39]
4
-Methoxy-4'-(trifluoromethyl)-1,1'-biphenyl (Table 2, entry 11)[36]
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