2492
Helvetica Chimica Acta – Vol. 89 (2006)
192.10. EI-MS: 240 (1, M+), 55 (49), 67 (17), 69 (55), 75 (18), 102 (41), 129 (100), 130 (19), 165 (15). HR-
EI-MS: 240.1511 (C17
N
N
(Phenylethynyl)cyclooctane (3d). IR (neat): 1448, 2198. 1H-NMR (500 MHz, CDCl3): 1.50–1.61 (m,
8 H, CH2); 1.72–1.83 (m, 4 H, CH2); 1.90–1.98 (m, 2 H, CH2); 2.79 (sept., J=4.13, CH); 7.23–7.28 (m, 3
arom. H); 7.37–7.38 (m, 2 arom. H). 13C-NMR (125 MHz, CDCl3): 23.66; 25.55; 27.54; 30.91; 31.72;
80.59; 95.50; 124.34; 127.43; 128.24; 131.67. EI-MS: 212 (212, M+), 91 (66), 115 (75), 129 (100), 141
(69), 155 (64). HR-EI-MS: 212.1561 (C
16Hþ20, M+; calc. 212.1565).
A
1
1-Cyclododecyl-3-phenylprop-2-yn-1-one (2e). IR (neat): 1665, 2199. H-NMR (500 MHz, CDCl3):
1.31–1.49 (m, 18 H, CH2); 1.66–1.73 (m, 2 H, CH2); 1.76–1.83 (m, 2 H, CH2); 2.72–2.78 (m, COCH);
7.37–7.41 (m, 2 arom. H); 7.43–7.47 (m, 1 arom. H); 7.56–7.59 (m, 2 arom. H). 13C-NMR (125 MHz,
CDCl3): 22.35; 23.40; 23.44; 23.54; 23.74; 23.83; 25.03; 25.90; 49.85; 87.47; 90.88; 120.45; 128.53;
130.52; 132.96; 191.93. EI-MS: 296 (5, M+), 55 (20), 69 (22), 102 (36), 129 (100), 130 (24). HR-EI-MS:
296.2139 (C
N
G
1
(Phenylethynyl)cyclododecane (3e). IR (neat): 1489, 2225. H-NMR (500 MHz, CDCl3): 1.25–1.61
(m, 16 H, CH2); 1.50–1.61 (m, 4 H, CH2); 1.65–1.73 (m, 2 H, CH2); 2.65–2.71 (m, CH); 7.22–7.28 (m,
3 arom. H); 7.37–7.40 (m, 2 arom. H). 13C-NMR (125 MHz, CDCl3): 22.20; 23.38; 23.45; 23.81; 23.88;
27.41; 29.91; 80.18; 94.93; 124.18; 127.32; 128.09; 131.56. EI-MS: 268 (28, M+), 91 (51), 115 (56), 128
(63), 129 (100). HR-EI-MS: 268.2193 (C
20Hþ28, M+; calc. 268.2191).
U
4-Ethyl-1-phenylhex-1-yn-3-one (2f) and 4-Methyl-1-phenylhept-1-yn-3-one (2f’). Ratio 2f/2f’ 29 :71.
IR (neat): 2199, 1667. 1H-NMR (500 MHz, CDCl3): 0.90–0.97 (m, 5.5 H, Me); 1.23 (d, J=6.85, 3 H, Me);
1.34–1.54 (m, 2.5 H, CH2); 1.59–1.68 (m, 1.1 H, CH2); 1.77–1.88 (m, 1.4 H, CH2); 2.42–2.48 (m, 0.4 H,
COCH); 2.67 (sext., J=5.95, 1.0 H, COCH); 7.31–7.47 (m, 4.2 H, Ph); 7.57–7.59 (m, 2.8 H, Ph). 13C-
NMR (100 MHz, CDCl3): 11.66; 14.06; 16.01; 20.26; 24.16; 35.05; 48.36; 57.70; 86.95; 87.04; 91.00;
91.33; 128.59; 130.59; 133.02; 133.07; 192.31. EI-MS: 200 (7, M+), 172 (22), 158 (39), 129 (100), 102
(76), 75 (100). HR-EI-MS: 200.1201 (C
N
N
(3-Ethylpent-1-ynyl)benzene (3f) and 1-(3-Methylhex-1-ynyl)benzene (3f’). Ratio 3f/3f’ 32 :68. IR
1
(neat): 2232. H-NMR (500 MHz, CDCl3): 0.94 (t, J=6.9, 3.0 H, Me); 1.06 (t, J=7.35, 2.7 H, Me); 1.24
(d, J=7.35, 3 H, Me); 1.40–1.63 (m, 5.8 H, CH2); 2.37–2.45 (m, 0.46 H, CH); 2.65 (sext., J=5.5, 1 H,
CH); 7.24–7.30 (m, 4 H, Ph); 7.37–7.42 (m, 2.9 H, Ph). 13C-NMR (125 MHz, CDCl3): 11.98; 14.03;
20.69; 21.14; 26.36; 27.85; 35.79; 39.28; 80.71; 81.97; 93.58; 94.91; 124.20; 127.45; 128.20; 131.60. EI-
MS: 172 (58, M+), 157 (56), 143 (87), 129 (100), 83 (90). HR-EI-MS: 172.1252 (C13H1þ6, M+; calc.
N
172.1248).
4-Ethyl-1-phenylhept-1-yn-3-one (2g) and 4-Methyl-1-phenyloct-1-yn-3-one (2g’). Ratio 2g/2g’ 43 :57.
IR (neat): 2200, 1670. 1H-NMR (400 MHz, CDCl3): 0.78–0.92 (m, 7.5 H, Me); 1.14 (d, J=7.1, 3 H, Me);
1.20–1.35 (m, 6.1 H, CH2); 1.40–1.60 (m, 2.1 H, CH2); 1.64–1.82 (m, 2.3 H, CH2); 2.42–2.49 (m, 0.75 H,
COCH); 2.53–2.64 (m, 1.0 H, COCH); 7.25–7.40 (m, 5.3 H, Ph); 7.47–7.55 (m, 3.5 H, Ph). 13C-NMR
(100 MHz, CDCl3): 11.66; 13.89, 14.12; 16.00; 20.43; 22.64; 24.62; 29.19; 32.57; 33.34; 48.54; 55.98;
128.57; 130.56; 132.99; 133.04; 192.29; 192.34. EI-MS: 214 (6, M+), 186 (11), 172 (48), 158 (49), 129
(100), 102 (39), 75 (21). HR-EI-MS: 214.1358 (C
N
N
(3-Ethylhex-1-ynyl)benzene (3g) and (3-Methylhept-1-ynyl)benzene (3g’) [16]. Ratio 3g/3g’ 43 :57. IR
(neat): 2228. 1H-NMR (400 MHz, CDCl3): 0.90–0.97 (m, 5.3 H, Me); 1.06 (t, J=7.32, 2.3 H, Me); 1.24 (d,
J=6.84, 3.0 H, CH2); 1.25–1.62 (m, 10.5 H, CH2); 2.44–2.54 (m, 0.8 H, CH); 2.58–2.66 (m, 1 H, CH);
7.25–7.32 (m, 5.3 H, Ph); 7.37–7.43 (m, 3.5 H, Ph). 13C-NMR (100 MHz, CDCl3): 11.88; 14.04; 14.68;
20.67; 21.11; 22.56; 26.49; 28.16; 29.65; 33.77; 36.72; 36.99; 41.59; 80.61; 81.73; 93.66; 94.89; 124.11;
124.22; 127.34; 127.38; 128.13; 131.55; 131.56. EI-MS: 186 (34, M+), 157 (47), 129 (100), 83 (77). HR-
EI-MS: 186.1409 (C14
C
0.90 (d, J=7.08, 2 Me); 1.16 (s, 2 Me); 2.25 (sept., J=4.55, Me2CH); 7.35–7.47 (m, 3 arom. H);
G
7.56–7.60 (m, 2 arom. H). 13C-NMR (125 MHz, CDCl3): 8.57; 17.54; 20.18; 33.97; 51.47; 86.49; 91.58;
120.35; 128.57; 130.47; 132.95; 194.80. EI-MS: 214 (12, M+), 84 (20), 85 (61), 102 (26), 129 (100), 130
(31), 143 (30), 199 (27). HR-EI-MS: 214.1353 (C15
U
G