The Journal of Organic Chemistry
Page 10 of 14
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CDCl3): δ 8.20-8.14 (m, 1H), 7.90-7.82 (m, 1H), 7.76 (d, J = 8.4 Hz, 1H), 7.51-7.42 (m, 3H), 7.37
(dd, J = 7.2, 1.2 Hz, 1H), 7.30-7.23 (m, 2H), 7.22-7.15 (m, 3H), 5.34 (ddt, J = 10.4, 3.4, 3.0 Hz, 1H),
2.83-2.70 (m, 2H), 2.46-2.37 (m, 4H), 1.50-1.34 (m, 4H), 0.91 (t, J = 7.2 Hz, 3H). 13C NMR (100
MHz, CDCl3): δ 203.3, 142.0, 137.3, 134.1, 131.5, 128.6, 128.5, 128.4, 127.3, 126.0, 125.8, 125.7,
125.5, 125.4, 104.4, 90.9, 35.8, 34.7, 31.0, 30.4, 22.6, 14.1. HRMS (ESI): m/z calcd. for
[C25H26Na]+ 349.1927, found 349.1922.
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3-(1-Phenylnona-3,4-dien-5-yl)thiophene (7g).
Following general method I, 7g was purified by flash column chromatography using pentane as
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eluent. The product was isolated as a pale yellow oil (23.6 mg) in 42% yield. H NMR (400 MHz,
CDCl3): δ 7.32-7.27 (m, 2H), 7.24-7.18 (m, 4H), 7.00-6.98 (m, 1H), 6.94 (dd, J = 5.0, 1.3 Hz, 1H),
5.49 (ddt, J = 10.2, 3.2, 2.8 Hz, 1H), 2.80 (dt, J = 7.1, 2.5 Hz, 2H), 2.50-2.40 (m, 2H), 2.34 (dt, J =
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7.3, 3.1 Hz, 2H), 1.53-1.44 (m, 2H), 1.44-1.35 (m, 2H), 0.94 (t, J = 7.3 Hz, 3H). C NMR (100
MHz, CDCl3): δ 204.0, 141.9, 139.5, 128.7, 128.5, 127.1, 126.0, 125.1, 118.5, 102.6, 93.4, 35.7,
31.2, 30.5, 30.1, 22.7, 14.2. HRMS (ESI): m/z calcd. for [C19H22SNa]+ 305.1334, found 305.1344.
Deca-3,4-diene-1,3-diyldibenzene (7h).
Following general method I, 7h was purified by flash column chromatography using pentane as
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eluent. The product was isolated as colorless oil (31.3 mg) in 54% yield. H NMR (400 MHz,
CDCl3): δ 7.47-7.45 (m, 2H), 7.37-7.28 (m, 4H), 7.28-7.19 (m, 4H), 5.54 (ddt, J = 10.4, 3.4, 3.0 Hz,
1H), 2.91-2.85 (m, 2H), 2.79-2.68 (m, 2H), 2.12-2.05 (m, 2H), 1.51-1.41 (m, 2H), 1.40-1.30 (m,
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6H), 0.92 (t, J = 6.9 Hz, 3H). C NMR (100 MHz, CDCl3): δ 204.0, 142.4, 137.5, 128.6, 128.5,
128.4, 126.5, 126.0, 126.0, 105.2, 95.3, 34.5, 32.0, 31.6, 29.2, 22.6, 14.2. HRMS (ESI): m/z calcd.
for [C22H26Na]+ 313.1927, found 313.1930.
(1-Cyclohexylidenehex-1-en-2-yl)benzene (7i).
Following general method I, 7i was purified by flash column chromatography using pentane as
eluent. The product was isolated as colorless oil (36.1 mg) in 75% yield. The spectral data is in
agreement with the corresponding literature values:30 1H NMR (400 MHz, CDCl3): δ 7.43-7.38 (m,
2H), 7.32-7.27 (m, 2H), 7.19-7.13 (m, 1H), 2.40 (t, J = 7.0 Hz, 2H), 2.26-2.18 (m, 4H), 1.74-1.64
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(m, 4H), 1.64-1.55 (m, 2H), 1.55-1.48 (m, 2H), 1.47-1.35 (m, 2H), 0.94 (t, J = 7.3 Hz, 3H). C
NMR (100 MHz, CDCl3): δ 198.3, 138.8, 128.3, 126.1, 126.0, 105.8, 103.2, 31.7, 30.3, 29.9, 28.0,
26.4, 22.5, 14.2. HRMS (APCI/TOF-Q) m/z: [M+H]+calcd. for C18H25 241.1951, found 241.1958.
(3-Methylnona-3,4-dien-5-yl)benzene (7j).
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