1
(55), 158 (24), 141 (36), 128 (29), 115 (15). H NMR (CDCl3)
Acknowledgements
δ: 2.42 (3H, s), 3.59 (1H, dd, J = 10.1, 11.4 Hz), 3.81–3.90 (2H,
m), 4.04–4.08 (2H, m), 5.25 (1H, br), 5.32 (1H, dd, J = 2.4, 10.0
Hz), 7.44 (1H, s), 7.49 (2H, d, J = 9.6 Hz), 8.02 (1H, d, J = 9.6
Hz), 8.20 (1H, d, J = 9.6 Hz). 13C NMR (CDCl3) δ: 15.64, 66.61,
67.60, 72.34, 74.67, 115.71, 121.82, 122.60, 124.38, 125.03,
125.78, 127.19, 130.96, 131.58, 148.62.
We thank the National Natural Science Foundation of China
(Grant No. 29972018) for financial support.
References
1 B. R. Arnold and J. C. Scaiano, J. Org. Chem., 1992, 57, 6469.
2 K. W. Field and G. B. Schurster, J. Org. Chem., 1988, 53, 4000.
3 W. Kirmse, R. Lelgemann and K. Friedrich, Chem. Ber., 1991, 124,
1853.
4 L. G. Plekhanova, G. A. Nikiforov, K. D. Jonge and V. V. Ershov,
Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 136.
5 G. F. Koser and W. H. Pirkle, J. Org. Chem., 1967, 32, 1992.
6 T. Kunitake and C. C. Price, J. Am. Chem. Soc., 1963, 85, 761.
7 J. K. Stille, P. Cassidy and L. Plummer, J. Am. Chem. Soc., 1963, 85,
1318.
8 G. A. Nikiforov, L. G. Plekhanova and V. V. Ershov, Izv. Akad. Nauk
SSSR, Ser. Khim., 1972, 1819.
9 T. Nozoe, T. Huang, M. Shyr, Y. Lin and H. Takeshita, Synlett,
1995, 952.
3Ј-Methyl-4Ј-oxo-1Ј,4Ј-dihydronaphthalene-1Ј-spiro-2-pyrane
(3bЈ). Colourless needles, mp: 88–89 ЊC. HR-SIMS: 229.1229
(C15H16O2 ϩ H, calc. 229.1223). EIMS (m/z, %): 228 (Mϩ, 100),
213 (50), 185 (78), 172 (29), 173 (29), 144 (48), 141 (31), 128
(35), 115 (98), 104 (45). 1H NMR (CDCl3) δ: 1.63 (1H, dd, J =
2.2, 13.4 Hz), 1.74–1.78 (1H, m), 1.82–1.86 (1H, m), 1.85 (2H,
dd, J = 2.2, 8.4 Hz), 2.02–2.06 (1H, m), 2.06 (3H, s), 4.01 (1H,
dd, J = 3.6, 12.1 Hz), 4.10 (1H, dd, J = 2.2, 12.1 Hz), 7.41
(1H, dd, J = 7.0, 7.6 Hz), 7.54 (1H, s), 7.60 (1H, dd, J = 7.0,
7.6 Hz), 7.79 (1H, d, J = 7.6 Hz), 8.08 (1H, d, J = 7.0 Hz).
13C NMR (CDCl3) δ: 16.69, 20.37, 25.58, 40.22, 62.33, 70.80,
126.27, 127.72, 129.70, 132.78, 134.23, 129.70, 140.41, 147.66,
184.85.
10 Y. S. Lin, S. Y. Jiang, T. C. Huang, S. J. Lin and Y. L. Chow, J. Org.
Chem., 1998, 63, 3364.
11 W. Sander, J. Org. Chem., 1988, 53, 2091.
12 G. Bucher and W. Sander, J. Org. Chem., 1992, 57, 1346.
13 W. Sander, G. Burcher, F. Reichel and D. Cremer, J. Am. Chem. Soc.,
1991, 113, 5311.
14 W. Sander, W. Muller and R. Sustmann, Angew. Chem., Int. Ed.
Engl., 1988, 27, 572.
2-Methyl-4-(tetrahydrofuran-2-yl)naphthol (4bЈ). Colourless
needles, mp: 126–127 ЊC. HR-SIMS: 229.1224 (C15H16O2 ϩ H,
calc. 229.1223). EIMS (m/z, %): 228 (Mϩ, 100), 213 (48), 185
1
(78), 171 (26), 172 (29), 158 (71), 128 (54), 115 (28). H NMR
(CDCl3) δ: 1.86–1.93 (1H, m), 2.03–2.10 (1H, m), 2.17 (3H, s),
2.44–2.53 (2H, m), 4.01 (1H, dd, J = 7.6, 14.0 Hz), 4.25 (1H, dd,
J = 7.6, 14.0 Hz), 5.25 (1H, br), 5.53 (1H, dd, J = 6.8, 6.9 Hz),
7.38 (1H, s), 7.45–7.48 (2H, m), 7.89–7.92 (1H, dd, J = 1.2, 9.7
Hz), 8.18 (1H, d, J = 10.2 Hz). 13C NMR (CDCl3) δ: 15.73,
25.97, 33.71, 68.54, 77.64, 115.50, 121.70, 123.80, 124.62,
124.85, 125.18, 125.29, 130.16, 130.97, 147.54.
15 D. Griller, A. S. Nazranand and J. C. Scaisano, J. Am. Chem. Soc.,
1984, 106, 198.
16 K. Motschiedler, P. Gudmundsdottir, J. P. Toscano, M. Platz and
M. A. Garcia-Garibay, J. Org. Chem., 1999, 64, 5139.
17 L. C. Anderson and M. J. Roedel, J. Am. Chem. Soc., 1945, 67,
955.
18 W. Ried and R. Dietrich, Chem. Ber., 1961, 94, 387.
19 H. H. Hodgson and E. W. Smith, J. Chem. Soc., 1935, 671.
1032
J. Chem. Soc., Perkin Trans. 2, 2002, 1029–1032