Wu et al.
1
6.0 Hz), 5.85 (1H, dd, J
dd, J ) 1.5 Hz, J ) 10.0 Hz), 7.00-7.02 (1H, m), 7.17-7.18
2H, m), 7.35-7.36 (1H, m); C{ H} NMR (125 MHz, CDCl
1
) 5.0 Hz, J
2
) 10.0 Hz), 6.43 (1H,
J
2
) 9.6 Hz), 6.55 (1H, dd, J
2
(1H, dd, J ) 2.8 Hz, J ) 9.6 Hz), 7.61-7.69 (4H, m), 8.25-
13 1
1
) 6.4 Hz, J
2
) 16.0 Hz), 7.44
1
2
1
1
3
1
(
3
)
8.35 (2H, m), 8.69-8.73 (2H, m); C{ H} NMR (100 MHz,
CDCl ) δ -1.09, 47.1, 66.1, 122.9, 123.1, 123.4, 123.8, 124.0,
δ 29.7, 33.4, 44.7, 70.2, 120.3, 126.1, 126.2, 127.1, 127.7, 127.9,
3
1
2
29.8, 132.5, 137.0, 147.4; HRMS (m/e) calcd for C16
H
20
O
126.0, 126.5, 126.6, 126.9, 127.1, 127.5, 128.7, 129.3, 129.8,
28.1514, found 228.1507.
24
129.9, 130.5, 130.6, 133.6, 144.2; HRMS (m/e) calcd for C23H -
2
-[(E)-3,3-Dimethyl-1-butenyl]-1,4-dimethyl-1,2-dihydro-
OSi 344.1596, found 344.1584.
1
R
-naphthalenol (3g): oil; TLC (hexane/ethyl acetate, 19:1)
f
Ethyl N-{2-[(E)-3,3-Dimethyl-1-butenyl]-1,2-dihydro-1-
1
) 0.38; H NMR (400 MHz, CDCl
3
) δ 0.95 (9H, s), 1.43 (3H,
) 5.6 Hz,
) 9.6 Hz), 5.71-5.77 (2H, m), 7.19-7.26 (3H, m), 7.58-
naphthalenyl}carbamate (3l): oil; TLC (hexane/ethyl ac-
etate, 19:1) R
1
s), 2.04 (4H, s), 2.77-2.81 (1H, m), 4.92 (1H, dd, J
J
7
2
1
2
1
f
) 0.21; H NMR (400 MHz, CDCl
3
) δ 0.95 (9H,
2
s), 1.23 (3H, t, J ) 7.2 Hz), 3.08-3.10 (1H, m), 4.11 (2H, Q, J
) 6.8 Hz, J ) 6.8 Hz), 4.91-5.01 (2H, m), 5.12 (1H, dd, J
7.2 Hz, J ) 16.0 Hz), 5.65 (1H, d, J ) 16.0 Hz), 5.92 (1H, dd,
) 4.8 Hz, J ) 9.6 Hz), 6.47 (1H, dd, J ) 1.2 Hz, J ) 9.6
Hz), 7.04-7.06 (1H, m), 7.19-7.24 (3H, m); C{ H} NMR (100
MHz, CDCl ) δ 14.6, 29.6, 33.2, 42.6, 51.8, 60.8, 120.4, 125.8,
126.3, 127.3, 127.6, 127.8, 130.1, 133.0, 135.1, 146.2, 156.4;
HRMS (m/e) calcd for C19 299.1885, found 299.1886.
2-[(E)-1-Ethyl-1-butenyl]-1,2-dihydro-1-naphthalenol
1
1
3
1
.60 (1H, m); C{ H} NMR (100 MHz, CDCl
3
) δ 19.1, 28.4,
2
1
)
9.7, 33.3, 51.8, 72.5, 121.1, 123.1, 124.1, 127.0, 127.2, 127.8,
2
30.7, 133.6, 142.8, 148.6; HRMS (m/e) calcd for C18
H
24
O
J
1
2
1
2
13
1
56.1827, found 256.1823.
6
-[(E)-3,3-Dimethyl-1-butenyl]naphtho[2,3-d][1,3]-
3
dioxole (3h): solid; mp 102-104 °C; TLC (hexane/ethyl
acetate, 19:1) R
1
f
) 0.18; H NMR (400 MHz, CDCl
3
) δ 1.14
H25NO
2
(
9H, s), 6.00 (2H, s), 6.32 (1H, d, J ) 16.0 Hz), 6.40 (1H, d, J
1
)
16.0 Hz), 7.05 (2H, s), 7.41-7.43 (1H, m), 7.54-7.58 (2H,
(4a): oil; TLC (hexane/ethyl acetate, 19:1) R
(400 MHz, CDCl ) δ 0.98 (3H, t, J ) 7.6 Hz), 1.00 (3H, t, J )
7.6 Hz), 1.93-1.98 (2H, m), 2.10-2.24 (3H, m), 3.28-3.30 (1H,
m), 4.61 (1H, dd, J ) 1.2 Hz, J ) 4.8 Hz), 5.50 (1H, t, J ) 3.6
Hz), 5.88 (1H, dd, J ) 4.0 Hz, J ) 8.0 Hz), 6.58 (1H, dd, J
2.4 Hz, J ) 7.2 Hz), 7.12-7.13 (1H, m), 7.22-7.29 (2H, m),
7.31-7.38 (1H, m); C{ H} NMR (100 MHz, CDCl
f
) 0.35; H NMR
1
3
1
m); C{ H} NMR (100 MHz, CDCl
3
) δ 29.5, 29.7, 33.4, 100.9,
03.8, 103.9, 122.6, 124.6, 126.7, 127.4, 129.5, 130.7, 134.2,
41.5, 147.2, 147.7; HRMS (m/e) calcd for C17 254.1307,
3
1
1
H
18
O
2
1
2
found 254.1308.
-[(E)-3,3-Dimethyl-1-butenyl]-1,2-dihydro-1-triphen-
ylenol (3i): oil; TLC (hexane/ethyl acetate, 19:1) R ) 0.25;
1
2
1
)
2
2
1
3
1
f
3
) δ 13.9,
1
H NMR (400 MHz, CDCl
Hz), 3.32-3.33 (1H, m), 5.33 (1H, dd, J
Hz), 5.85-5.90 (2H, m), 6.22 (1H, dd, J
2
Hz), 7.41 (1H, dd, J ) 2.8 Hz, J ) 9.6 Hz), 7.64-7.71 (4H,
13 1
3
) δ 1.13 (9H, s), 1.82 (1H, d, J ) 6.8
14.7, 21.2, 47.2, 47.5, 67.8, 126.6, 127.4, 127.8, 128.3, 128.7,
1
) 2.0 Hz, J
) 2.8 Hz, J
2
) 6.0
) 9.6
20
129.7, 130.0, 132.5, 135.3, 138.4; HRMS (m/e) calcd for C16H O
1
2
228.1514, found 228.1514.
1
m), 8.25-8.34 (2H, m), 8.70-8.74 (2H, m); C{ H} NMR (100
MHz, CDCl ) δ 29.8, 33.3, 44.3, 66.7, 122.6, 122.9, 123.0, 123.3,
Acknowledgment. We thank the National Science
3
Council of the Republic of China (NSC 92-2113-M-007-
0
1
1
3
23.7, 123.9, 124.1, 124.3, 126.3, 126.5, 126.7, 126.8, 127.0,
44) for support of this research.
24
27.2, 129.9, 130.5, 131.2, 145.2; HRMS (m/e) calcd for C24H O
28.1827, found 328.1831.
Supporting Information Available: Spectral data for
2
-[(E)-2-(1,1,1-Trimethylsilyl)-1-ethenyl]-1,2-dihydro-1-
1
compounds 3b-f,j and 4b,c and H NMR spectra for all
compounds. This material is available free of charge via the
Internet at http://pubs.acs.org.
triphenylenol (3k): oil; TLC (hexane/ethyl acetate, 19:1) R
f
1
)
0.28; H NMR (400 MHz, CDCl
J ) 6.0 Hz), 3.39-3.41 (1H, m), 5.42 (1H, dd, J
6.0 Hz), 6.17 (1H, d, J ) 16.0 Hz), 6.28 (1H, dd, J
3
) δ 0.19 (9H, s), 1.82 (1H, d,
) 2.0 Hz, J
) 2.8 Hz,
1
2
)
1
JO048721U
8412 J. Org. Chem., Vol. 69, No. 24, 2004