P. H. Lee et al.
(m,1H),1.38 ppm (t,
J=7.2 Hz,6H); 13C NMR (100 MHz,CDCl
,
(4-Methylenehept-6-enyl)benzene (45): Rf =0.6 (hexane); 1H NMR
(400 MHz,CDCl 3,25 8C,TMS): d=7.30–7.26 (m,2H),7.19–7.16 (m,
3H),5.81 (ddt, J=16.95,10.12,6.95 Hz,1H),5.07–5.02 (m,2H),4.78 (s,
3
258C): d=166.5,150.8,142.3,129.7,129.0,127.2,113.8,60.7,43.1,20.5,
14.3 ppm; IR (film): n˜ =2978,1726,1610,1587,1415,1392,1367,916,
584 cmÀ1
204.1146.
; HRMS (EI): m/z: calcd for C13H16O2: 204.1150; found:
2H),2.76 (d, J=6.88 Hz,2H),2.61 (t,
7.53 Hz,2H),1.77 ppm (quin,
J=7.68 Hz,2H); 13C NMR (100 MHz,
CDCl3,25 8C): d=147.89,142.49,136.44,128.43,128.28,125.69,116.09,
110.16,40.76,35.54,29.35 ppm; IR (film): n˜ =3049,2976,2310,1431,
1257 cmÀ1; HRMS (EI): m/z: calcd for C14H18: 186.1409; found: 186.1408.
J=7.69 Hz,2H),2.07 (t,
J=
Ethyl 4-(but-2-enyl)benzoate (37): (cis and trans mixture): Rf =0.3
(hexane/EtOAc 30:1); 1H NMR (400 MHz,CDCl 3,25 8C,TMS): d=1.38
(t, J=7.1 Hz,3H),1.69 (d, J=4.75 Hz,3H; trans),1.69 (d, J=1.07 Hz,
3H; cis),3.35 (d, J=4.61 Hz,2H; trans),3.45 (d, J=6.2 Hz,2H; cis),
4.36 (q, J=7.13 Hz,2H),5.53–5.58 (m,2H),7.21–7.98 ppm (m,4H);
13C NMR (100 MHz,CDCl 3,25 8C): d=166.6,146.5,146.4,129.7,129.6,
129.0,128.4,128.2,128.2,128.0,127.1,125.6,77.64,77.01,76.37,60.70,
2-Allylnaphthalene (46): Rf =0.5 (hexane); 1H NMR (400 MHz,CDCl
258C,TMS): d=7.86–7.77 (m,3H),7.63 (s,1H),7.49–7.40 (m,3H),7.33
(dd, J=8.46,1.42 Hz,1H),6.05 (ddt, J=16.98,10.09,6.77 Hz,1H),5.16–
,
3
5.11 (m,2H),3.55 ppm (d, J=6.66 Hz,2H); 13C NMR (100 MHz,CDCl ,
3
39.0 (trans),33.12 ( cis),17.8 ( trans),14.3,12.8 ppm ( cis); IR (film): n˜ =
3023,2856,1716,1610,761,701 cm
C13H16O2 (264.12): C 76.4,H 7.9; found: C 76.3,H 7.8.
258C): d=137.55,137.32,133.65,132.12,128.04,127.62,127.48,127.39,
À1; elemental analysis calcd (%) for
126.66,125.93,125.27,40.36 ppm; IR (film):
n˜ =3003,2916,1684,1606,
1414,1358 cm À1; HRMS (EI): m/z: calcd for C13H12: 168.0939; found
168.0934.
Ethyl 4-(2-methylprop-2-enyl)benzoate (38): Rf =0.3 (hexane/EtOAc
30:1); 1H NMR (400 MHz,CDCl 3,25 8C,TMS): d=1.39 (t, J=7.2 Hz,
4-Allyl-8-methoxy-1,2-dihydronaphthalene (47): Rf =0.5 (hexane/EtOAc
30:1); 1H NMR (400 MHz,CDCl 3,25 8C,TMS): d=7.15 (d, J=7.86 Hz,
1H),6.92 (d, J=7.86 Hz,1H),6.79 (d, J=8.20 Hz,1H),5.95 (ddt, J=
3H),1.67 (s,3H),3.37 (s,2H),4.37 (q,
J=7.2 Hz,2H),4.74 (s,1H),4.84
(s,1H),7.26 (d, J=8.2 Hz,2H),7.97 ppm (d, J=8.2 Hz,2H); 13C NMR
(100 MHz,CDCl 3,25 8C): d=14.3,22.0,44.6,60.8,112.6,128.4,128.9,
16.70,10.17,6.35 Hz,1H),5.90–5.88 (m,1H),5.11 (dd,
J=17.16,1.58 Hz,
J=6.36,
129.6,144.2,145.1,166.6 ppm; IR (film):
mental analysis calcd (%) for C13H16O2 (204.12): C 76.4,H 7.9; found: C
76.2,H 7.9.
Ethyl 3-allylbenzoate (39): Rf =0.3 (hexane/EtOAc 30:1); 1H NMR
(400 MHz,CDCl 3,25 8C,TMS): d=7.88 (m,2H),7.36 (m,2H),5.97
n˜ =1711,1652,706 cm À1; ele-
1H),5.06 (dd, J=10.07,1.58 Hz,1H),3.83 (s,3H),3.18 (dd,
1.28 Hz,2H),2.76 (t, J=8.07 Hz,2H),2.27–2.21 ppm (m,2H); 13C NMR
(100 MHz,CDCl 3,25 8C): d=156.02,136.79,135.91,134.47,126.17,
124.40,115.96,115.89,109.46,55.48,37.37,22.53,19.89 ppm; IR (film):
À1
n˜ =3054,2986,1573,1422,1263 cm
; HRMS (EI): m/z: calcd for
C14H16O: 200.1201; found 200.1202.
(ddt, J=6.61,9.22,15.96 Hz,1H),5.09 (d,
10.04 Hz,1H),4.37 (q,
J=15.62 Hz,1H),5.10 (d, J=
J=6.64 Hz,2H),
J=7.10 Hz,2H),3.44 (d,
Ethyl 2-allylcyclohexene-1-carboxylate (48): Rf =0.3 (hexane/EtOAc
30:1); 1H NMR (400 MHz,CDCl 3,25 8C,TMS): d=5.83 (ddt, J=16.95,
10.11,6.67 Hz,1H),5.07–4.99 (m,2H),4.19 (q,
J=6.63 Hz,2H),2.33–2.25 (m,2H),2.26–2.08 (m,2H),1.63–1.57 (m,
4H),1.29 ppm (t, J=7.11 Hz,3H); 13C NMR (100 MHz,CDCl 3,25 8C):
d=168.98,146.02,136.10,125.52,115.68,60.02,39.89,30.74,26.55,22.27,
22.25,14.30 ppm; IR (film): n˜ =2991,1721,1642,1453,1245 cm À1; HRMS
(EI): m/z: calcd for C12H18O2: 194.1307; found 194.1306.
1.39 ppm (t, J=7.20 Hz,3H); 13C NMR (100 MHz,CDCl 3,25 8C): d=
167.12,140.71,137.22,133.53,131.03,130.08,127.85,127.78,116.76,61.34,
40.34,14.75 ppm; IR (film): n˜ =3054,2986,1714,1422,1266 cm À1; HRMS
(EI): m/z: calcd for C12H14O2: 190.0994; found: 190.0994.
J=7.11 Hz,2H),3.10 (d,
Ethyl 3-(2-methylprop-2-enyl)benzoate (40): Rf =0.3 (hexane/EtOAc
30:1); 1H NMR (400 MHz,CDCl 3,25 8C,TMS): d=7.90–7.87 (m,2H),
7.38–7.34 (m,2H),4.84 (s,1H),4.73 (s,1H),4.38 (q,
3.37 (s,2H),1.68 (s,3H),1.68 (s,3H),1.40 ppm (t,
J=7.10 Hz,2H),
J=7.12 Hz,3H);
1-Allyl-4-(tert-butyl)cyclohexene (49): Rf =0.5 (hexane); 1H NMR
13C NMR (100 MHz,CDCl 3,25 8C): d=166.79,144.54,140.05,133.41,
130.53,130.03,128.29,127.41,112.44,60.93,44.36,22.06,14.35 ppm; IR
(film): n˜ =2980,2937,1719,1281,1191 cm À1; HRMS (EI): m/z: calcd for
C13H16O2: 204.1150; found: 204.1158.
(400 MHz,CDCl ,25 8C,TMS): d=5.80 (ddt, J=16.1,9.96,6.89 Hz,1H),
3
5.43 (d, J=3.61 Hz,1H),5.02 (d, J=15.33 Hz,1H),4.99 (d, J=8.31 Hz,
1H),2.68 (d, J=6.66 Hz,2H),2.05–1.74 (m,5H),1.26–1.12 (m,2H),
0.86 ppm (s,9H); 13C NMR (100 MHz,CDCl 3,25 8C): d=136.99,136.14,
122.08,115.41,44.15,42.01,32.20,29.83,27.25,26.87,24.26 ppm; IR
1-Allyl-4-trifluoromethylbenzene (41): Rf =0.5 (hexane); 1H NMR
(400 MHz,CDCl 3,25 8C,TMS): d=7.69 (d, J=8.1 Hz,2H),7.44 (d, J=
(film): n˜ =3054,2862,2305,1637,1423,1267 cm
À1; HRMS (EI): m/z:
8.1 Hz,2H),6.20–6.00 (m,1H),5.30–5.20 (m,2H),3.58 ppm (d,
J=
calcd for C13H22: 178.1721; found: 178.1717.
6.6 Hz,2H); 13C NMR (100 MHz,CDCl 3,25 8C): d=143.9,136.0,128.9,
128.6,124.1,116.3,39.6 ppm; IR (film): n˜ =3050,2960,1650 cm À1; HRMS
(EI): m/z: calcd for C10H9F3: 186.0656; found: 186.0656.
3-Methylene-4-vinylcyclopentane-1,1-dicarboxylic acid diethyl ester (61):
Rf =0.5 (hexane/EtOAc 20:1); 1H NMR (400 MHz,CDCl 3,25 8C,TMS):
d=5.09–5.05 (m,2H),4.98 (d, J=2.20 Hz,1H),4.82 (d, J=2.20 Hz,1H),
4.20 (q, J=7.18 Hz,2H),4.19 (q, J=7.18 Hz,2H),3.20–3.14 (m,1H),
3.07 (d, J=17.5 Hz,1H),2.94 (dq, J=17.5,2.30 Hz 1H),2.57 (dd, J=
4-Allylnitrobenzene (42): Rf =0.3 (hexane/EtOAc 20:1); 1H NMR
(400 MHz,CDCl 3,25 8C,TMS): d=8.16 (d, J=8.72 Hz,2H),7.35 (d, J=
8.51 Hz,2H),5.95 (ddt, J=6.68,10.52,16.94 Hz,1H),5.18–5.10 (m,2H),
3.49 ppm (d, J=6.65 Hz,2H); 13C NMR (100 MHz,CDCl 3,25 8C): d=
13.0,7.65 Hz,1H),2.00 (dd,
J=13.0,10.9 Hz,1H),1.26 (t,
J=7.08 Hz,
3H),1.25 ppm (t, J=7.08 Hz,3H); 13C NMR (100 MHz,CDCl 3,25 8C):
d=171.76,171.57,150.62,139.17,116.01,107.96,61.55,61.53,58.58,
47.72,40.18,14.04 ppm; IR (film): n˜ =2982,1732,1658,1640,1465,1446,
1266,1189 cm À1; HRMS (EI): m/z: calcd for C14H20O4: 252.1362; found:
252.1361.
147.79,146.54,135.46,129.38,123.68,117.41,39.89 ppm; IR (film):
n˜ =
3080,2919,1604,1519,1494,1347 cm
À1; HRMS (EI): m/z: calcd for
C9H9NO2: 163.0633; found: 163.0636.
2-Phenylpenta-1,4-diene (43): Rf =0.5 (hexane); 1H NMR (400 MHz,
CDCl3,25 8C,TMS): d=7.44 (d, J=7.15 Hz,2H),7.36–7.42 (m,3H),
3-Vinylindan-1-carboxylic acid ethyl ester (63): Rf =0.3 (hexane/EtOAc
10:1); Isomer A ; 1H NMR (400 MHz,CDCl 3,25 8C,TMS): d=7.39 (d,
5.94–5.86 (m,1H),5.39 (s,1H),5.12 (d,
J=13.69 Hz,1H),5.10 (s,1H),
J=6.49 Hz,2H); 13C NMR
5.07 (d, J=8.60 Hz,1H),3.25 ppm (d,
J=7.10 Hz,1H),7.26–7.21 (m,2H),5.85 (ddd,
J=8.84,8.90,17.26 Hz,
(100 MHz,CDCl 3,25 8C): d=146.33,140.94,136.20,128.25,127.44,
1H),5.24–5.09 (m,2H),4.28–4.20 (m,2H),4.07–4.00 (m,2H),2.58 (ddd,
125.99,116.46,113.15,39.51 ppm; IR (film):
n˜ =3053,2986,2305,1422,
J=7.76,7.76,12.87,Hz,1H),2.23 (ddd,
J=9.46,9.46,12.86 Hz,1H),
1265 cmÀ1; HRMS (EI): m/z: calcd for C11H12: 144.0939; found: 144.0935.
trans-1-Phenylpenta-1,4-diene (44): Rf =0.5 (hexane); 1H NMR
1.32 ppm (t, J=7.11 Hz,3H); 13C NMR (100 MHz,CDCl 3,25 8C): d=
173.47,145.52,140.66,140.59,127.54,127.01,125.00,124.48,115.77,60.89,
49.12,48.73,36.07,14.35 ppm; Isomer B;
258C,TMS): d=7.39 (d, J=7.10 Hz,1H),7.26–7.21 (m,2H),5.85 (ddd,
J=8.84,8.90,17.26 Hz,1H),5.24–5.09 (m,2H),4.15 (q, J=7.17 Hz,2H),
4.07–4.00 (m,1H),3.74 (q, J=8.50 Hz,1H),2.71 (ddd, J=12.94,7.89,
1H NMR (400 MHz,CDCl
,
(400 MHz,CDCl 3,25 8C,TMS): d=7.36–7.19 (m,5H),6.41 (d,
15.90 Hz,1H),6.23 (dt, J=15.77,6.66 Hz,1H),5.96–5.86 (m,1H),5.11
(d, J=17.13 Hz,1H),5.07 (d, J=10.12 Hz,1H),2.96 ppm (t, J=7.04 Hz,
2H); 13C NMR (100 MHz,CDCl 3,25 8C): d=137.62,136.47,130.85,
J=
3
128.49,128.18,127.02,126.04,115.67,37.00 ppm; IR (film):
n˜ =3053,
3.68 Hz,1H),2.10 (ddd, J=8.18,8.18,13.05 Hz,1H),1.26 ppm (t,
J=
7.10 Hz,3H); 13C NMR (100 MHz,CDCl 3,25 8C): d=173.72,145.79,
À1
2986,2395,1421,1270 cm
;
HRMS (EI): m/z: calcd for C11H12
:
144.0939; found: 144.0935.
140.66,140.39,127.76,127.01,124.76,124.48,115.44,60.81,49.12,48.67,
5204
ꢀ 2007 Wiley-VCH Verlag GmbH & Co. KGaA,Weinheim
Chem. Eur. J. 2007, 13,5197 – 5206