JOURNAL OF CHEMICAL RESEARCH 2009 581
The Raney Ni–Al alloy was acquired commercially from Jinzhou
Catalyst Company (Jinzhou, P.R. China).
1,2-Bis(2-methoxyphenyl)ethane (4i):13 1H NMR: d = 2.88 (4H,
s), 3.84 (6H, s, 2OCH3), 6.84–7.16 (8H, m); dC (67.8 MHz, CDCl3)
= 30.90, 55.62, 110.52, 120.68, 127.54, 130.22, 131.24 and 157.94;
GC/MS (m/z): 242 (M+), 211, 180, 121 and 77.
General procedure
1,2-Bis(4-methoxyphenyl)ethane (4k):13 1H NMR: d = 2.86 (4H,
s), 3.72 (6H, s, 2 OCH3), 6.88 (2H, d, J = 8.4 Hz), 7.12 (2H, d,
J = 8.4 Hz); dC (67.8 MHz, CDCl3) = 30.9, 56.0, 126.5, 130.4, 132.2
and 154.4; GC/MS (m/z): 242 (M+), 211, 180, 121 and 77.
1,2-Bis(4-tert-butylphenyl)ethane (4l):13b 1H NMR: d = 1.35 (18H,
s, 2But), 2.96 (4H, s), 7.12 (2H, d, J = 8.2 Hz), 7.32 (2H, d, J = 8.2 Hz);
dC (67.8 MHz, CDCl3) = 22.2, 34.2, 40.2, 126.5, 130.4, 137.3 and
141.8; GC/MS (m/z): 294 (M+), 237, 180, 147, 77 and 57.
1,2-Bis(4-aminophenyl)ethane (4m):14 1H NMR: d = 2.76 (4H, s),
3.60 (4H, bs, NH2), 6.66 (2H, d, J = 8.4 Hz), 7.02 (2H, d, J = 8.4
Hz); dC (67.8 MHz, CDCl3) = 20.0, 125.3, 131.1, 134.2, and 144.6;
GC/MS (m/z): 242 (M+), 106 and 77.
An aq. 1w% KOH solution (40 mL) was added over 1.0 hour and
at 90°C, to a mixture of 1a (2.1 g, 10.0 mmol), Raney Ni–Al alloy
(4.0 g) and water (40 mL). After the mixture had been heated for an
additional 6 h at 90°C, it was cooled to rt and filtered over celite.
The residue was washed with ethyl acetate. The filtrate was neutralised
with hydrochloric acid and extracted with ethyl acetate (3 ¥ 15 mL).
The organic layer was dried over anhydrous magnesium sulfate and
the solvent was removed. A mixture of 1,2-dicyclohexylethane (2a),
1-cyclohexyl-2-phenylethane (3a), 1,2-diphenylethane (4a) was
obtained in the ratio of 60.4: 26.3: 13.3, according to GC-analysis
(Table 1, run 2). Compounds 2a, 3a and 4a were separated by column
chromatography on silica gel by using hexane as solvent.
1,2-Dicyclohexylethane (2a):7 1H NMR: d = 0.60–0.72 (4H, m),
1.02–1.14 (6H, m), 1.22–1.32 (2H, m), 1.42–1.62 (10H, m), 2.29 (4H,
d, J = 6.4 Hz); GC/MS (m/z): 194 (M+), 110, 96, 83, 67, 55 and 41.
1-Cyclohexyl-2-phenylethane (3a):12 1H NMR: d = 0.78–1.00 (2H,
m), 1.20–1.35 (4H, m), 1.55–1.60 (2H, m), 1.70–1.86 (5H, m), 2.60
(2H, t, J = 6.0 Hz), 6.96–7.15 (2H, m), 7.20–7.26 (3H, m); GC/MS
(m/z): 188 (M+), 92, 83, 77, 67, 55 and 41.
1,3-Diphenylpropane (4n):15 1H NMR: d = 1.72 (2H, t, J = 6.7 Hz),
2.66 (4H, t, J = 6.7 Hz), 7.16–7.26 (6H, m), 7.24–7.32 (4H, m);
dC (67.8 MHz, CDCl3) = 31.3, 35.9, 125.8, 128.4, 128.6 and 142.7;
GC/MS (m/z): 196 (M+), 119, 91 and 77.
1,4-Diphenylbutane (4o):15 1H NMR: d = 1.68 (4H, dt, J = 7.0 Hz),
2.62 (4H, t, J = 7.0 Hz), 7.12–7.22 (6H, m), 7.20–7.28 (4H, m);
dC (67.8 MHz, CDCl3) = 31.2, 35.9, 125.7, 128.3, 128.7 and 142.3;
GC/MS (m/z): 210 (M+), 105 and 77.
1,3-Dicyclohexylpropane (2n):15 1H NMR: d = 0.60–0.72 (4H, m),
1.06–1.30 (12H, m), 1.40–1.60 (10H, m), 2.26 (2H, t, J = 6.8 Hz);
dC (67.8 MHz, CDCl3) = 26.2, 27.0, 28.2, 33.0, 36.1, 37.5; GC/MS
(m/z): 208 (M+), 124, 110, 67, 55 and 41.
1,5-Diphenylpentane (4p):16 1H NMR: d = 1.22 (2H, t, J = 3.6 and
7.0 Hz), 1.66 (4H, m), 2.56 (4H, t, J = 7.0 Hz), 7.16–7.26 (6H, m),
7.24–7.32(4H, m); dC (67.8 MHz, CDCl3) = 28.62, 31.30, 35.66,
125.15, 128.32, 128.55 and 142.10; GC/MS (m/z): 224 (M+), 119, 105
and 77.
1-Cyclohexyl-3-phenylpropane (3n):18 1H NMR: d = 0.66–0.78
(2H, m), 1.08–1.24 (6H, m), 1.52–1.72 (7H, m), 2.32 (2H, t, J = 6.9
Hz), 7.00–7.15 (2H, m), 7.22–7.30 (3H, m); dC (67.8 MHz, CDCl3)
= 26.4, 27.2, 28.8, 33.2, 36.3, 37.3, 37.8, 125.6, 128.0, 128.6, 143.1;
GC/MS (m/z): 202 (M+), 106, 97, 77, 67, 55 and 41.
1,6-Diphenylhexane (4q):17 1H NMR: d = 1.22 (4H, dt, J = 3.6
and 7.0 Hz), 1.62 (4H, m), 2.52 (4H, t, J = 6.8 Hz), 7.10–7.20
(6H, m), 7.12–7.22 (4H, m); dC (67.8 MHz, CDCl3) = 29.2, 31.3,
35.9, 125.7, 128.2, 128.7 and 141.9; GC/MS (m/z): 238 (M+), 119,
105 and 77.
1,4-Dicyclohexylbutane (2o):15 1H NMR: d = 0.60–0.72 (4H, m),
1.02–1.32 (12H, m), 1.42–1.62 (10H, m), 2.24 (4H, t, J = 6.6 Hz);
dC (67.8 MHz, CDCl3) = 26.4, 27.2, 28.6, 33.2, 36.0, 37.8; GC/MS
(m/z): 222 (M+), 138, 124, 112, 67, 55 and 41.
1-Cyclohexyl-4-phenylbutane (3o):19 1H NMR: d = 0.64–0.76 (2H,
m), 1.06–1.22 (8H, m), 1.50–1.70 (7H, m), 2.30 (2H, t, J = 6.9 Hz),
7.04–7.18 (2H, m), 7.24–7.32 (3H, m); dC (67.8 MHz, CDCl3) = 26.6,
26.9, 27.0, 32.2, 33.7, 36.3, 37.7, 38.3, 126.2, 128.4, 128.6, 143.2;
GC/MS (m/z): 216 (M+), 120, 106, 67, 55 and 41.
All of the compounds 2, 3 and 4 were compared with authentic
samples and their structures were assigned on the basis of IR,
1H NMR and GC-MS spectroscopic data.
1,5-Dicyclohexylpentane (2p):16 1H NMR: d = 0.60–0.72 (4H, m),
1.00–1.30 (14H, m), 1.44–1.64 (12H, m), 2.23 (2H, t, J = 6.8 Hz);
dC (67.8 MHz, CDCl3) = 26.0, 27.4, 28.3, 33.0, 36.2, 37.4, 38.4; GC/
MS (m/z): 236 (M+), 150, 136, 124, 112, 67, 55 and 41.
Published online: 8 September 2009
1-Cyclohexyl-5-phenylpentane (3p): 1H NMR: d = 0.62–0.75 (2H,
m), 1.04–1.20 (10H, m), 1.52–1.70 (7H, m), 2.27 (2H, t, J = 6.8 Hz),
7.02–7.16 (2H, m), 7.22–7.30 (3H, m); dC (67.8 MHz, CDCl3) = 26.6,
26.9, 27.0, 32.2, 33.7, 36.3, 37.7, 38.3, 39.2, 126.0, 128.1, 128.3,
143.0; GC/MS (m/z): 230 (M+), 134, 120, 106, 67, 55 and 41.
1,6-Dicyclohexylhexane (2q):17 1H NMR: d = 0.58–0.70 (4H, m),
1.00–1.30 (14H, m), 1.44–1.64 (12H, m), 2.23 (4H, t, J = 6.8 Hz);
dC (67.8 MHz, CDCl3) = 26.1, 27.3, 28.0, 33.2, 36.6, 37.1, 38.2; GC/
MS (m/z): 250 (M+), 164, 150, 138, 124, 112, 67, 55 and 41.
1-Cyclohexyl-6-phenylhexane (3q): 1H NMR: d = 0.62–0.75 (2H,
m), 1.04–1.20 (12H, m), 1.50–1.71 (7H, m), 2.20 (2H, t, J = 6.6 Hz),
7.00–7.15 (2H, m), 7.22–7.28 (3H, m); dC (67.8 MHz, CDCl3) = 26.4,
26.7, 27.2, 32.4, 33.4, 36.5, 37.6, 38.1, 39.0, 39.6, 126.2, 128.3, 128.1,
143.1; GC/MS (m/z): 244 (M+), 148, 134, 120, 106, 67, 55 and 41.
1,2-Diphenylethane (4a):10 1H NMR: d = 2.92 (4H, s), 7.18–7.22
(6H, m), 7.22–7.32 (4H, m); dC (67.8 MHz, CDCl3) = 38.3, 126.4,
128.6, 128.9 and 142.2; GC/MS (m/z): 182 (M+), 91 and 77.
1,2-Bis(4-methylphenyl)ethane (4h):13 1H NMR: d = 2.36 (6H, s,
2CH3), 2.90 (4H, s), 7.05 (4H, d, J = 8.2 Hz), 7.22 (4H, d, J = 8.2 Hz);
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