1058
R. E. Barrientos-Astigarraga et al. / Tetrahedron 58 (2002) 1051±1059
37, 4741. (b) Barrientos-Astigarraga, R. E.; Moraes, D. N.;
Comasseto, J. V. Tetrahedron Lett. 1999, 40, 265.
5. Casson, S.; Kocienski, P. Organometallic Reagents in
Organic Synthesis; Batesson, J. H., Mitchell, M. B., Eds.;
Academic: London, 1994; Vol. 7, pp 129±159.
(30 min). To this solution, cooled to 08C, was added the
enolphosphate 13a (0.35 g, 1.5 mmol) and the mixture
was stirred at room temperature for 5 h. Then ethyl acetate
(50 mL) was added and the organic phase was washed with
brine (3£50 mL). The solvents were evaporated and the
residue was puri®ed by silica gel column chromatography
eluting with hexane/ethyl acetate (9/1).
6. (a) Uemura, S.; Fukuzawa, S. I.; Patil, S. R. J. Organomet.
Chem. 1983, 243, 9. (b) Ogawa, A.; Tsuboi, Y.; Obayashi, R.;
Yokoyama, K.; Ryu, I.; Sonoda, N. J. Org. Chem. 1994, 59,
1600. (c) Chief®, A.; Comasseto, J. V. Tetrahedron Lett. 1994,
35, 4063. (d) Chief®, A.; Comasseto, J. V. Synlett 1995, 671.
(e) Zeni, G.; Comasseto, J. V. Tetrahedron Lett. 1999, 40,
4619. (f) Dabdoub, M. J.; Dabdoub, V. B.; Marino, J. P.
Tetrahedron Lett. 2000, 41, 433. (g) Dabdoub, M. J.;
Dabdoub, V. B.; Marino, J. P. Tetrahedron Lett. 2000, 41, 437.
7. (a) Buzilova, S. R.; Vereshchagin, L. I.; Sadekov, I. D.;
Minkin, V. I. J. Org. Chem. (USSR) 1976, 46, 932. For reviews
see: (b) Comasseto, J. V. Rev. Heteroatom Chem. 1993, 9, 61.
(c) Petragnani, N. Tellurium in Organic Synthesis; Academic:
London, 1994. (d) Comasseto, J. V.; Lo, W. L.; Petragnani, N.;
Stefani, H. A. Synthesis 1997, 373.
5.5.1. (Z)-4-[(2-Thienyl)telanyl]-3-penten-2-one (11k). 1H
NMR (CDCl3, 500 MHz) d (ppm) 7.53±7.52 (m, 1H);
7.41±7.40 (m, 1H); 7.30 (d, J1.2 Hz, 1H); 7.04±7.02
(m, 1H); 2.25 (s, 3H); 2.15 (d, J1.2 Hz, 3H); 13C NMR
(CDCl3, 125 MHz) d (ppm) 197.2; 159.8; 141.9; 134.5;
128.8; 109.5; 29.4; 27.1; 125Te NMR (CDCl3, 157.79
MHz) d (ppm) 716; LR-MS m/z (rel. int.): 296 (79)(M1);
292 (42); 213 (44); 83 (100); 51 (8); IR (neat) n (cm21
)
3089; 3073; 1638; 1528; 1361; 1211; 1108; 843; 708;
629; Anal. calcd for C9H10OSTe: C, 36.79; H, 3.43;
Found: C, 37.19; H, 3.40.
8. Zeni, G.; Formiga, H. B.; Comasseto, J. V. Tetrahedron Lett.
2000, 41, 1311.
Acknowledgements
9. For a review see: (a) Rappoport, Z. Acc. Chem. Res. 1992, 25,
479. For a recent report on the vinylic substitution mechanism
see: (b) Bernasconi, C. F.; Kittredge, K. W.; Flores, F. X.
J. Org. Chem. 1999, 64, 2897.
The authors thank the following agencies for support: CNPq
and FAPESP.
10. Dabdoub, M. J.; Dabdoub, V. M.; Comasseto, J. V.;
Petragnani, N. J. Organomet. Chem. 1986, 308, 211.
11. Ohe, K.; Takahashi, H.; Uemura, S.; Sugita, N. Nippon
Kagaku Kaishi 1987, 1469.
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