(w). 1H NMR (300 MHz): δ 3.00 (s, 6H, N(CH3)2), 3.09 (dd, 1H, 2J6,6=15.5, 3J6,7=7.3 Hz, one of H-6),
2
5
2
3.11 (dd, 1H, J5a,5b=14.5, J5a,6=2.1 Hz, H-5a), 3.37 (d, 1H, J9,9=13.2 Hz, one of H-9), 3.54 (d, 1H,
2
2
3
2J5b,5a=14.5 Hz, H-5b), 3.86 (d, 1H, J9,9=13.2 Hz, the other of H-9), 4.20 (ddd, 1H, J6,6=15.5, J6,7=4.7,
5J6,5a=1.9 Hz, the other of H-6), 4.90 (s, 1H, H-2), 5.00 (dd, 1H, 3J8b,7=16.8, 2J8b,8a=0.9 Hz, H-8b), 5.10
(dd, 1H, 3J8a,7=9.9, 2J8a,8b=0.7 Hz, H-8a), 5.63 (m, 1H, H-7), 6.72–7.36 (m, 9H, arom. CH). 13C NMR (75
MHz): δ 40.6 (N(CH3)2), 42.6 (C-6), 55.1 (C-5), 56.1 (C-9), 81.6 (C-2), 112.2–137.2 (arom. CH and Cq),
118.0 (C-8), 132.4 (C-7), 170.8 (C-4, C=O). EI-MS; m/z (%): 335.5 (1) [M+], 293.5 (3), 292.5 (8), 291.3
(17), 216.5 (11), 215.2 (88), 201.0 (17), 117.6 (13), 92.1 (6), 90.9 (100), 64.8 (8), 40.8 (9). Anal. Calcd
for C21H25N3O: C 75.19 H 7.51 N 12.53. Found C 75.11 H 7.48 N 12.50.
3-Allyl-1-benzyl-2-(4-nitrophenyl)imidazolidin-4-one (3d): Flash chromatography (1:1) – White
crystals, mp 93-94o C (petroleum ether/ethyl acetate). IR (KBr): ν-1 = 3080 (w), 3064 (w), 3029 (w), 2924
(w), 2811 (w), 1711 (s), 1524 (s), 1434 (m), 1348 (s), 1315 (m), 801 (m), 701 (m). 1H NMR (300 MHz):
δ 3.04 (dd, 1H, 2J6,6=15.5, 3J6,7=7.6 Hz, one of H-6), 3.26 (dd, 1H, 2J5a,5b=14.5, 5J5a,6=2.0 Hz, H-5a), 3.58
2
2
2
(d, 1H, J9,9=13.2 Hz, one of H-9), 3.69 (d, 1H, J5b,5a=14.5 Hz, H-5b), 3.81 (d, 1H, J9,9=13.2 Hz, the
2
3
5
other of H-9), 4.29 (ddd, 1H, J6,6=15.5, J6,7=4.6, J6,5a=1.7 Hz, the other of H-6), 4.96 (dd, 1H,
3J8b,7=17.2, 2J8b,8a=0.8 Hz, H-8b), 5.11 (s, 1H, H-2), 5.15 (dd, 1H, 3J8a,7=10.2, 2J8a,8b=0.7 Hz, H-8a), 5.62
(m, 1H, H-7), 7.17–8.28 (m, 9H, arom. CH). 13C NMR (75 MHz): δ 42.9 (C-6), 55.0 (C-5), 57.0 (C-9),
80.6 (C-2), 119.0 (C-8), 124.0–145.0 (arom. CH and Cq), 131.8 (C-7), 170.6 (C-4, C=O). EI-MS; m/z
(%): 337.4 (1) [M+], 291.5 (41), 263.2 (6), 216.3 (9), 215.1 (100), 201.1 (15), 118.0 (12), 90.9 (84), 64.8
(7), 40.9 (11). Anal. Calcd for C19H19N3O3: C 67.64 H 5.68 N 12.46. Found C 67.44 H 5.59 N 12.32.
3-Allyl-2-(2-allyoxyphenyl)-1-benzylimidazolidin-4-one (3e): Flash chromatography (1:3) – Slightly
yellow oil. IR (NaCl): ν-1 = 3079 (w), 3066 (w), 3029 (w), 2919 (w), 2852 (w), 2804 (w), 1707 (s), 1598
1
(w), 1490 (m), 1434 (m), 1284 (w), 1240 (m), 1097 (w), 1020 (w), 755 (m), 700 (m). H NMR (300
2
3
2
5
MHz): δ 3.24 (dd, 1H, J6,6=15.5, J6,7=7.8 Hz, one of H-6), 3.22 (dd, 1H, J5a,5b=14.5, J5a,6=1.7 Hz,
H-5a), 3.56 (d, 1H, 2J9,9=13.2 Hz, one of H-9), 3.63 (d, 1H, 2J5b,5a=14.5 Hz, H-5b), 3.87 (d, 1H, 2J9,9=13.2
2
3
5
Hz, the other of H-9), 4.20 (ddd, 1H, J6,6=15.5, J6,7=5.3, J6,5a=1.7 Hz, the other of H-6), 4.58 (d, 1H,
3J=5.0 Hz, OCH2CH=CH2), 5.01 (d, 1H, 3J8b,7=17.2 Hz, H-8b), 5.06 (d, 1H, 3J8a,7=10.9 Hz, H-8a), 5.34
(dd, 1H, 3J=10.6, 2J=1.7 Hz, OCH2CH=CH2), 5.46 (dd, 1H, 3J=17.5, 2J=1.7 Hz, OCH2CH=CH2), 5.67 (s,
13
1H, H-2), 6.10 (m, 1H, OCH2CH=CH2), 6.91–7.57 (m, 9H, arom. CH). C NMR (75 MHz): δ 42.8
(C-6), 55.1 (C-5), 56.7 (C-9), 69.1 (OCH2CH=CH2), 74.7 (C-2), 111.9–157.7 (arom. CH and Cq), 117.6 and
117.7 (C-8 and OCH2CH=CH2), 132.3 and 133.1 (C-7 and OCH2CH=CH2), 171.1 (C-4, C=O). EI-MS;