J = 7.8 Hz); 13C-NMR (CDCl3, 125.8 MHz): δ 35.9; 114.1; 114.2; 116.6; 117.4; 126.0; 126.7; 127.7;
128.3; 140.3; 145.7; 147.7; 149.4. Anal. Calcd for C15H14O2: C, 79.62; H, 6.24. Found: C, 79.36; H, 6.12.
1
trans-Hex-1-enylhydroquinone (8a): yield 96%; colourless crystals; mp 106 °C; H-NMR (DMSO-d6,
300.13 MHz): δ 0.90 (t, 3H, J = 7.0 Hz), 1.37 (m, 4H), 2.15 (q, 2H, J = 6.9 Hz), 6.05 (m, 1H), 6.44 (dd,
1H, J = 8.55, 2.9 Hz), 6.53 (d, 1H, J = 16 Hz, 1'-H), 6.60 (d, 1H, J = 8.6 Hz, 6-H), 6.73 (d, 1H,
J = 2.8 Hz), 8.60 (s, 1H), 8.74 (s, 1H); 13C-NMR (DMSO-d6, 75.5 MHz): δ 13.7; 21.6; 31.1; 32.4; 111.6;
114.5; 116.1; 124.4; 124.7; 129.4; 146.7; 149.7. Anal. Calcd for C12H16O2: C, 81.34; H, 5.12. Found: C,
81.12; H, 4.98.
trans-2,5-Dihydroxystilbene (8b)5: yield 98%; mp 165-167; 13C-NMR (CDCl3, 75.5 MHz): δ 111.4;
115.2; 116.1; 123.4; 124.0; 125.6; 126.4; 127.0; 127.8; 137.3; 147.4; 149.4.
1
2-(2,2-Diphenylvinyl)hydroquinone (8c)6: brown oil; yield 68%; H-NMR (CDCl3, 300.13 MHz): δ
6.12 (d, 1H, J = 2.8 Hz), 6.39 (dd, 1H, J = 8.6, 2.9 Hz), 6.58 (d, 1H, J = 8.6 Hz), 7.00 (s, 1H), 7.20 (m,
10H), 7.83 (s, 1H), 8.23 (s, 1H); 13C-NMR (CDCl3, 75.5 MHz): δ 114.8; 115.3; 115.5; 123.4; 124.5;
126.5; 127.1; 127.3; 127.6; 129.8; 139.8; 140.7; 143.2; 148.2; 148.5.
cis-3-Methylchromane-2,6-diol (9a): yellow oil; yield 12%; 1H-NMR (DMSO-d6/CDCl3, 500.13 MHz):
δ 0.96 (d, 3H, J = 6.8 Hz), 1.88 (m, 1H), 2.41 (dd, 1H, J = 16.0, 5.5 Hz), 2.50 (dd, 1H, J = 15.8, 5.8 Hz),
5.18 (d, 1H, J = 2.2 Hz), 6.39 (s, 1H), 6.46 (m, 1H), 6.47 (m, 1H); 13C-NMR (DMSO-d6/CDCl3,
125.8 MHz): δ 15.8; 27.9; 31.0; 93.4; 111.8; 113.7; 116.3; 122.2; 144.2; 150.4. Anal. Calcd for C10H12O3:
C, 66.65; H, 6.71. Found: C, 66.49; H, 6.68.
trans-3-Methylchromane-2,6-diol (9b): yellow oil; yield 12%; 1H-NMR (DMSO-d6/CDCl3,
500.13 MHz): δ 0.90 (d, 3H, J = 6.9 Hz), 1.89 (m, 1H), 2.25 (dd, 1H, J = 9.8, 6.1 Hz), 2.83 (dd, 1H,
13
J = 9.7, 5.8 Hz), 4.94 (d, 1H, J = 4.8 Hz), 6.39 (s, 1H), 6.44 (m, 1H), 6.46 (m, 1H); C-NMR (DMSO-
d6/CDCl3, 125.8 MHz): δ 15.9; 29.0; 31.0; 95.9; 111.8; 113.7; 116.2; 121.4; 144.7; 150.4. Anal. Calcd for
C10H12O3: C, 66.65; H, 6.71. Found: C, 66.49; H, 6.68.
1
2-Methyl-2-vinylcoumaran-5-ol (10): yield 10%; light brown oil; H-NMR (CDCl3, 500.13 MHz): δ
1.54 (s, 3H), 2.94 (d, 1H, J = 15.8 Hz), 3.08 (d, 1H, J = 15.8 Hz), 5.10 (d, 1H, J = 10.5 Hz, vinyl-CH ),
2
5.30 (d, 1H, J = 17.6 Hz), 6.03 (dd, 1H, J = 17.4, 10.7 Hz), 6.62 (m, 1H), 6.65 (m, 1H), 6.71 (m, 1H); 13C-
NMR (CDCl3, 125.8 MHz): δ 25.6; 42.0; 87.7; 109.2; 112.5; 112.7; 114.25; 127.4; 141.2; 149.4; 142.5.
Anal. Calcd for C11H12O2: C, 74.98; H, 6.86. Found: C, 74.77; H, 6.72.
1
2-Isopropenylcoumaran-5-ol (11): yield 42%; light brown oil; H-NMR (CDCl3, 500.13 MHz): δ 1.75
(s, 3H), 2.95 (dd, 1H, J = 15.9, 9.0 Hz), 3.22 (dd, 1H, J = 15.9, 9.0 Hz), 4.70 (s, 1H), 5.09 (s, 1H), 5.13 (t,
13
1H, J = 8.9 Hz), 6.63 (m, 2H), 6.73 (m, 1H); C-NMR (CDCl3, 125.8 MHz): δ 16.9; 34.7; 85.7; 108.9;