2
430
L.-S. Li, Y.-L. Wu / Tetrahedron Letters 43 (2002) 2427–2430
3
4
. Wu, W.-L.; Yao, Z.-J.; Li, Y.-L.; Li, J.-C.; Xia, Y.; 8. Pakulski, Z.; Zamojski, A. Tetrahedron 1997, 53, 2653–
Wu, Y.-L. J. Org. Chem. 1995, 60, 3257.
2666.
. (a) For a general review, see: Haines, A. H. In Methods
for the Oxidation of Organic Compounds; Academic
Press: London, 1985, p. 153; (b) Che, C.-M.; Yu, W.-
Y.; Chan, P.-M.; Cheng, W.-C.; Peng, S.-M.; Lau, K.-
C.; Li, W.-K. J. Am. Chem. Soc. 2000, 122,
9. (a) Srinivasan, N. S.; Lee, D. G. J. Org. Chem. 1979,
44, 1574; (b) Lee, D. G.; Chang, V. S. J. Org. Chem.
1979, 44, 2726–2730.
10. Tatlock, J. H. J. Org. Chem. 1995, 60, 6221–6223.
11. The alkynyl ethers Tatlock used were synthesized by
the reaction of the corresponding electrophiles with
lithioethoxyacetylene according to the methods reported
by Raucher (Raucher, S.; Bray, B. L. J. Org. Chem.
1987, 52, 2332–2333).
1
1380–11392; (c) Dayan, S.; Ben-David, I.; Rozen, S. J.
Org. Chem. 2000, 65, 8816–8818; (d) Walsh, C. J.;
Mandal, B. K. J. Org. Chem. 1999, 64, 6102–6105; (e)
Pr a¨ ler, O. C.; Sauer, J. Tetrahedron Lett. 1998, 39,
8
821; (f) Zibuck, R.; Seebach, D. Helv. Chim. Acta
12. Tanaka, R.; Rodgers, M.; Simonaitis, R.; Miller, S. I.
1
988, 71, 237–240; (g) Torii, S.; Inokuchi, T.; Hirata,
Tetrahedron 1971, 27, 2651–2669.
13. The NMR data of 7: H NMR (300 MHz, CDCl
1
Y. Synthesis 1987, 377–379; (h) Lee, D. G.; Lee, E. J.;
Brown, K. C. ACS Symp. Ser. 1987, 326, 82–95; (i)
Wolfe, S.; Ingold, C. F. J. Am. Chem. Soc. 1983, 105,
3
): l
3.90 (2H, t, J=6.6 Hz), 3.69 (3H, s), 2.54 (2H, t, J=
1
3
6.6 Hz), 0.89 (9H, s), 0.06 (6H, s). C NMR (75 MHz,
CDCl ): l 172.2, 59.1, 51.5, 37.9, 25.8 (3C), 18.2, −5.5
7
755.
. (a) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60,
728–7732; (b) Eisaku, N.; Hisaji, T.; Yoshio, O. Bull.
3
+
+
5
(2C). EIMS (m/z, %): 219 (M +1, 8.46), 203 (M −Me,
38.65), 187 (41.36), 161 (100.00). IR (film): 2951, 1742,
1259, 1170, 1021, 842 cm .
7
−
1
Chem. Soc. Jpn. 1994, 67, 309–311; (c) Ishii, Y.;
Sakata, Y. J. Org. Chem. 1990, 55, 5545–5547; (d) Bal-
listreri, F. P.; Failla, S.; Spina, E.; Tomaselli, G. A. J.
Org. Chem. 1989, 54, 947–949; (e) Ballistreri, F. P.;
Failla, S.; Tomaselli, G. A. Stud. Org. Chem. (Amster-
dam), 1988, 33 (Role Oxygen Chem. Biochem.), 341–
14. (a) Simandi, L. I.; Jaky, M. Tetrahedron Lett. 1970,
3489–3492; (b) Lee, D. G.; Lee, E. J.; Chandler, W. D.
J. Org. Chem. 1985, 50, 4306–4309.
1
15. The NMR data of 8: H NMR (300 MHz, CDCl
): l
3
3.96 (2H, t, J=6.0 Hz), 3.86 (3H, s), 3.04 (2H, t, J=
13
3
46; (f) Moriarty, R. M.; Penmasta, R.; Awasthi, A.
6.0 Hz), 0.86 (9H, s), 0.05 (6H, s). C NMR (75 MHz,
CDCl ): l 194.1, 162.3, 58.4, 53.1, 42.5, 25.9 (3C), 18.3,
K.; Prakash, I. J. Org. Chem. 1988, 53, 6124–6125; (g)
Ballistreri, F. P.; Failla, S.; Tomaselli, G. A. J. Org.
Chem. 1988, 53, 830–831; (h) Mueller, P.; Godoy, J.
Helv. Chim. Acta 1981, 64, 2531–2533.
3
+
−5.6 (2C). EIMS (m/z, %): 245 (M −1, 1.35), 205
(1.98), 159 (38.46), 89 (51.57), 75 (100.00), 43 (10.21).
IR (film): 2957, 2859, 1758, 1733, 1465, 1258, 1110,
−
1
6
. Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27,
836, 778 cm . Elemental analysis calcd for C11
C, 53.66; H, 8.94. Found: C, 53.97; H, 8.87.
H O Si:
22 4
1
947–1950.
. Chen, C.; Crich, D. J. Chem. Soc., Chem. Commun.
991, 1289–1290.
7
16. Hu, T.-S.; Wu, Y.-L.; Wu, Y. Org. Lett. 2000, 2, 887–
1
889.