1346 J . Org. Chem., Vol. 64, No. 4, 1999
Notes
amount of the above freshly prepared W(CO)5‚THF (0.1 M in
THF solution) was added to a substrate, and the mixture was
stirred for 3-5 days at room temperature under an Ar atmo-
sphere. The reaction was quenched with pH 7 phosphate buffer,
and the organic materials were extracted with ethyl acetate
three times. The combined extracts were dried over MgSO4. After
removal of the solvent, the residue was purified by preparative
TLC to give the corresponding cyclized product. Spectral data
of the products 2, 4, 8, and 16 coincided with those of the
commercially available materials.
7.52 (1H, d, J ) 5.3 Hz), 7.52-7.54 (1H, m), 7.58-7.61 (1H, m),
7.75 (1H, d, J ) 8.6 Hz), 7.84 (1H, d, J ) 8.6 Hz), 7.95 (1H, d,
J ) 8.1 Hz), 8.17 (1H, d, J ) 8.1 Hz); 13C NMR (CDCl3) 122.0,
123.6, 125.0, 125.0, 125.2, 125.2, 125.5, 125.6, 126.6, 128.8, 129.0,
130.7, 137.3.
Na p h th o[2,1-b]th iop h en e (22):11 IR (KBr disk) 3067, 1263,
1113, 806 cm-1 1H NMR (CDCl3) δ 7.51-7.54 (1H, m), 7.58-
;
7.62 (2H, m), 7.74 (1H, d, J ) 8.7 Hz), 7.88 (1H, d, J ) 8.7 Hz),
7.94 (1H, d, J ) 8.4 Hz), 7.99 (1H, d, J ) 5.3 Hz), 8.33 (1H, d,
J ) 8.4 Hz); 13C NMR (CDCl3) 120.6, 122.0, 123.6, 125.0, 125.2,
125.8, 126.4, 128.5, 129.3, 130.9, 135.9, 137.3.
1-(ter t-Bu tyld im eth ylsiloxy)n a p h th a len e (6): IR (neat)
3302, 2931, 2858, 1626, 1473, 1306 cm-1 1H NMR (CDCl3) δ
;
Na p h th o[1,2-b]-1-m eth ylp yr r ole (24): IR (KBr disk) 3057,
2971, 2916, 1504, 1354 cm-1 1H NMR (CDCl3) δ 4.29 (3H, s),
;
0.32 (6H, s), 1.13 (9H, s), 6.89 (1H, d, J ) 7.6 Hz), 7.34 (1H, t,
J ) 7.8 Hz), 7.46-7.49 (3H, m), 7.81-7.83 (1H, m), 8.21-8.23
(1H, m); 13C NMR (CDCl3) -4.2, 18.5, 25.9, 112.6, 120.9, 122.6,
125.1, 125.9, 126.1, 127.6, 128.0, 135.1, 151.7; HRMS calcd for
6.63 (1H, d, J ) 2.9 Hz), 7.07 (1H, d, J ) 2.9 Hz), 7.44-7.46
(1H, m), 7.52-7.56 (2H, m), 7.72-7.74 (1H, m), 7.97-7.98 (1H,
m), 8.48-8.50 (1H, m); 13C NMR (CDCl3) 38.5, 102.1, 120.6,
120.9, 121.1, 123.3, 123.4, 125.1, 125.8, 129.0, 129.2, 129.9, 131.3.
Anal. Calcd for C13H11N: C, 86.15; H, 6.12; N, 7.73. Found: C,
85.86; H, 6.19; N, 7.82.
C
16H22OSi 258.1419, found 258.1425.
Eth yl 1-Meth yl-2-n a p h th a len eca r boxyla te (12): IR (neat)
3062, 2933, 1716, 1624, 1466, 1277, 1238 cm-1; 1H NMR (CDCl3)
δ 1.43 (3H, t, J ) 7.1 Hz), 2.93 (3H, s), 4.42 (2H, q, J ) 7.1 Hz),
7.52-7.57 (2H, m), 7.69-7.71(1H, m), 7.80-7.84 (2H, m), 8.17-
8.18 (1H, m); 13C NMR (CDCl3) 14.4, 15.8, 61.1, 125.3, 125.8,
126.1, 126.5, 127.2, 128.3, 128.5, 132.9, 134.6, 136.8, 168.9;
HRMS calcd for C14H14O2 214.0994, found 214.0993.
Ack n ow led gm en t. We are grateful to Professor
Koichi Narasaka (University of Tokyo) for helpful
discussion during this work. This work was supported
by Grant-in-Aid for Scientific Research on Priority Areas
(No. 283, Innovative Synthetic Reactions and No. 706,
Dynamic Control of Stereochemistry) from the Ministry
of Education, Science, Sports and Culture, Government
of J apan. K.M. has been granted a Research Fellowship
of the J apan Society for the Promotion of Science for
Young Scientists.
1-(t er t -B u t y ld im e t h y ls ilo x y )-2-m e t h y ln a p h t h a le n e
(14): IR (neat) 2960, 2931, 1599, 1385, 1255 cm-1 1H NMR
;
(CDCl3) δ -0.06 (6H, s), 0.96 (9H, s), 2.41 (3H, s), 7.25-7.29
(1H, m), 7.39-7.49 (3H, m), 7.76-7.78 (1H, m), 8.07-8.08 (1H,
m); 13C NMR (CDCl3) -3.1, 17.5, 18.7, 26.1, 121.3, 122.7, 123.0,
124.7, 124.9, 127.5, 128.2, 129.6, 133.6, 148.4; HRMS calcd for
C13H15OSi 215.0892 (M-t-Bu), found 215.0891.
Na p h th o[1,2-b]fu r a n (18):9 IR (neat) 1510, 1392, 1321, 810
cm-1 1H NMR (CDCl3) δ 6.90 (1H, d, J ) 2.0 Hz), 7.47-7.49
;
(1H, m), 7.57-7.60 (1H, m), 7.65 (2H, s), 7.76 (1H, d, J ) 2.0
Hz), 7.93 (1H, d, J ) 8.2 Hz), 8.31 (1H, d, J ) 8.2 Hz); 13C NMR
(CDCl3) 107.6, 119.7, 120.0, 121.5, 122.9, 123.4, 125.0, 126.3,
128.3, 131.4, 144.1, 150.5.
Su p p or tin g In for m a tion Ava ila ble: Procedures for the
preparation of the precursors of the cyclization. This material
Na p h th o[1,2-b]th iop h en e (20):10 IR (KBr disk) 3051, 1323,
J O981361O
1259, 810 cm-1 1H NMR (CDCl3) δ 7.48 (1H, d, J ) 5.3 Hz),
;
(10) Clark, P. D.; McKinnon, D. M. Can. J . Chem. 1981, 59, 1297.
(11) Clark, P. D.; McKinnon, D. M. Can. J . Chem. 1981, 59, 227.
(9) Narasimhan, N. S.; Mali, R. S. Tetrahedron 1975, 31, 1005.