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T. Di Franco et al.
FEATURE ARTICLE
1H NMR (400 MHz, CDCl3): δ = 7.45–7.15 (m, 2 H), 7.09–6.76 (m,
3 H), 3.98 (t, J = 6.6 Hz, 2 H), 1.81 (dt, J = 14.6, 6.6 Hz, 2 H), 1.67–
1.41 (m, 4 H), 1.41–1.12 (m, 12 H), 0.91 (t, J = 6.9 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 159.3, 129.5, 120.6, 114.6,
68.0, 32.1, 29.8, 29.7, 29.6, 29.50, 29.47, 26.2, 22.9, 14.3.
1-Bromo-4-decylbenzene (3j)
Colorless oil; yield: 97 mg (65%).
1H NMR (400 MHz, CDCl3): δ = 7.38 (d, J = 8.0 Hz, 2 H), 7.06 (t,
J = 9.6 Hz, 2 H), 2.55 (t, J = 7.5 Hz, 2 H), 1.71–1.48 (m, 2 H), 1.48–
1.13 (m, 14 H), 1.03–0.70 (m, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 142.0, 131.4, 128.4, 119.4,
35.5, 32.1, 31.5, 29.9, 29.8, 29.7, 29.6, 29.5, 29.3, 22.8, 14.3.
HRMS (APCI): m/z [M]+ calcd for C17H28O: 248.2140; found:
248.2148.
HRMS (APCI): m/z [M]+ calcd for C16H25Br: 296.1140; found:
296.1149.
Anal. Calcd for C17H28O: C, 82.20; H, 11.36. Found: C, 82.34; H,
11.56.
Anal. Calcd for C16H25Br: C, 64.64; H, 8.48. Found: C, 67.35; H,
9.14.
Phenyl(undecyl)sulfane (3f)
White solid; yield: 71 mg (54%); mp 29–30 °C.
1H NMR (400 MHz, CDCl3): δ = 7.31 (t, J = 7.9 Hz, 2 H), 7.27 (d,
J = 4.2 Hz, 2 H), 7.16 (t, J = 6.9 Hz, 1 H), 2.92 (t, J = 7.3 Hz, 2 H),
1.76–1.59 (m, 2 H), 1.48–1.37 (m, 2 H), 1.37–1.16 (m, 14 H), 0.88
(t, J = 6.3 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 129.0, 128.9, 125.8, 33.7,
32.1, 29.8, 29.7, 29.6, 29.5, 29.32, 29.31, 29.0, 22.8, 14.3.
1-Chlorotetradecane (3k)
Colorless oil; yield: 67 mg (58%).
1H NMR (400 MHz, CDCl3): δ = 3.53 (t, J = 6.6 Hz, 2 H), 1.91–
1.66 (m, 2 H), 1.64–1.12 (m, 22 H), 0.88 (t, J = 6.0 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 45.4, 32.8, 32.1, 29.83,
29.81, 29.7, 29.6, 29.5, 29.1, 27.1, 22.9, 14.3.
HRMS (APCI): m/z [M]+ calcd for C17H28S: 264.1912; found:
264.1904.
Anal. Calcd for C14H29Cl: C, 72.22; H, 12.55. Found: C, 72.19; H,
12.56.
Anal. Calcd for C17H28S: C, 77.21; H, 10.67. Found: C, 77.35; H,
10.69.
1,4-Diphenylbutane (4a)
Colorless liquid; yield: 80 mg (76%).
1H NMR (400 MHz, CDCl3): δ = 7.32 (t, J = 7.2 Hz, 4 H), 7.26–
7.06 (m, 6 H), 2.69 (m, 4 H), 1.73 (m, 4 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 142.7, 128.5, 128.4, 36.0,
31.2.
HRMS (APCI): m/z [M]+ calcd for C16H18: 210.1409; found:
210.1411.
2-Undecylfuran (3g)
Colorless oil; yield: 58 mg (52%).
1H NMR (400 MHz, CDCl3): δ = 7.44–7.11 (m, 1 H), 6.27 (s, 1 H),
5.96 (s, 1 H), 2.80–2.38 (m, 2 H), 1.79–1.56 (m, 2 H), 1.48–0.98 (m,
16 H), 0.96–0.71 (m, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 156.8, 140.7, 110.2, 104.6,
32.1, 29.79, 29.78, 29.71, 29.53, 29.50, 29.4, 28.2, 28.1, 22.9, 14.3.
Anal. Calcd for C16H18: C, 91.37; H, 8.63. Found: C, 90.28; H, 8.61.
HRMS (APCI): m/z [M]+ calcd for C15H26O: 222.1984; found:
222.1990.
(3-Phenoxypropyl)benzene (4e)
Yellow oil; yield: 92 mg (87%).
Anal. Calcd for C15H26O: C, 81.02; H, 11.79. Found: C, 81.05; H,
11.85.
1H NMR (400 MHz, CDCl3): δ = 7.34–7.33 (m, 4 H), 7.28–7.26 (m,
3 H), 7.01–6.94 (m, 3 H), 4.01 (t, J = 6.0 Hz, 2 H), 2.87 (t, J = 7.2
Hz, 2 H), 2.18–2.14 (m, 2 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 159.2, 141.7, 129.6, 128.7,
128.5, 126.1, 120.7, 114.67, 66.9, 32.3, 31.0.
HRMS (APCI): m/z [M]+ calcd for C15H16O: 212.1201; found:
212.1207.
1-(1-Undecyl-1H-pyrrol-2-yl)ethan-1-one (3h)
Yellow oil; yield: 65 mg (49%).
1H NMR (400 MHz, CDCl3): δ = 7.04–6.95 (m, 1 H), 6.95–6.82 (m,
1 H), 6.19–6.06 (m, 1 H), 4.32 (t, J = 7.2 Hz, 2 H), 2.45 (s, 3 H),
1.83–1.67 (m, 2 H), 1.48–1.08 (m, 16 H), 0.90 (t, J = 6.4 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 188.3, 130.3, 123.7, 120.3,
107.9, 50.0, 44.1, 32.1, 31.6, 29.74, 29.72, 29.5, 29.4, 27.5, 26.8,
22.8, 14.3.
Anal. Calcd for C15H16O: C, 84.87; H, 7.60. Found: C, 82.73; H,
7.59.
HRMS (ESI): m/z [M + H]+ calcd for C17H30NO: 264.2327; found:
264.2329.
Phenyl(3-phenylpropyl)sulfane (4f)
Yellow oil; yield: 23 mg (20%).
Anal. Calcd for C17H29NO: C, 77.51; H, 11.10; N, 5.32. Found: C,
77.44; H, 11.05; N, 5.61.
1H NMR (400 MHz, CDCl3): δ = 7.46–7.26 (m, 6 H), 7.26–7.07 (m,
4 H), 2.96 (t, J = 7.1 Hz, 2 H), 2.80 (t, J = 7.3 Hz, 2 H), 2.01 (p,
J = 7.1 Hz, 2 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 141.4, 136.7, 129.3, 129.0,
128.6, 128.5, 126.0, 34.8, 33.1, 30.8.
HRMS (APCI): m/z [M]+ calcd for C15H16S: 228.0973; found:
228.0980.
9-Undecyl-9H-carbazole (3i)
Colorless oil; yield: 114 mg (71%).
1H NMR (400 MHz, CDCl3): δ = 8.12 (d, J = 7.6 Hz, 2 H), 7.47 (d,
J = 7.2 Hz, 2 H), 7.46–7.35 (m, 2 H), 7.30–7.18 (m, 2 H), 4.31 (m,
7.2 Hz, 2 H), 2.01–1.79 (m, 2 H), 1.50–1.12 (m, 16 H), 0.89 (t,
J = 6.5 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 140.6, 125.7, 123.0, 120.5,
118.8, 108.8, 43.2, 32.0, 29.7, 29.65, 29.57, 29.45, 29.1, 27.5, 22.8,
14.3.
Anal. Calcd for C15H16S: C, 78.90; H, 7.06. Found: C, 78.96; H,
7.03.
1-Methoxy-4-octylbenzene (4o)
Colorless oil; yield: 21 mg (19%).
1H NMR (400 MHz, CDCl3): δ = 7.09 (d, J = 8.0 Hz, 2 H), 6.82 (d,
J = 8.1 Hz, 2 H), 3.79 (s, 3 H), 2.54 (t, J = 7.7 Hz, 2 H), 1.59 (m, 2
H), 1.29–1.26 (m, 10 H), 0.87 (t, J = 10.8 Hz, 3 H).
HRMS (APCI): m/z [M]+ calcd for C23H31N: 321.2457; found:
321.2450.
Anal. Calcd for C23H31N: C, 85.92; H, 9.72; N, 4.36. Found: C,
86.23; H, 9.71; N, 4.51.
13C{1H} NMR (100 MHz, CDCl3): δ = 157.7, 135.2, 113.8, 55.4,
35.2, 32.1, 31.9, 29.7, 29.4, 22.8, 14.3.
Synthesis 2013, 45, 2949–2958
© Georg Thieme Verlag Stuttgart · New York