C. C. Sil6eira et al. / Tetrahedron Letters 44 (2003) 5703–5705
5705
Synthesis 1997, 221–228; (e) Silveira, C. C.; Perin, G.;
Braga, A. L.; Petragnani, N. Synlett 1995, 58–60.
23. Lee, C. W.; Koh, Y. J.; Oh, D. Y. J. Chem. Soc., Perkin
10. (a) Huang, Y. Z.; Mo, X. S. Synlett 1998, 93–95; (b) Mo,
X. S.; Huang, Y. Z. Tetrahedron Lett. 1995, 36, 3539–
3542; (c) Dabdoub, M. J.; Begnini, M. L.; Cassol, T. M.;
Guerrero, P. G., Jr.; Silveira, C. C. Tetrahedron Lett.
1995, 36, 7623–7626; (d) Hiiro, T.; Kambe, N.; Ogawa,
A.; Miyoshi, N.; Murai, S.; Sonoda, N. Angew. Chem.,
Int. Ed. Engl. 1987, 26, 1187–1188; (e) Barros, S. M.;
Comasseto, J. V.; Berriel, J. N. Tetrahedron Lett. 1989,
30, 7353–7356; (f) Comasseto, J. V.; Berriel, J. N. Synth.
Commun. 1990, 20, 1681–1685; (g) Barros, S. M.; Dab-
doub, M. J.; Dabdoub, V. B.; Comasseto, J. V.
Organometallics 1989, 8, 1661–1665; (h) Ogawa, A.;
Tsuboi, Y.; Obayashi, R.; Yokoyama, K.; Ryu, I.;
Sonoda, N. J. Org. Chem. 1994, 59, 1600–1601; (i) Dab-
doub, M. J.; Dabdoub, V. B. Tetrahedron 1995, 51,
9839–9850; (j) Dabdoub, M. J.; Jacob, R. G.; Ferreira, J.
T. B.; Dabdoub, V. B.; Marques, F. A. Tetrahedron Lett.
1999, 40, 7159–7162; (k) Dabdoub, M. J.; Dabdoub, V.
B.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 2261–
2264; (l) Dabdoub, M. J.; Dabdoub, V. B.; Guerrero, P.
G., Jr.; Silveira, C. C. Tetrahedron 1997, 53, 4199–4218.
11. Huang, Y. Z.; Mo, X. S. Tetrahedron Lett. 1998, 39,
1945–1948.
Trans. 1 1994, 717–719.
24. Preparation of the telluromethyldiphenylphosphine oxide 2:
To a solution of LDA (10 mmol) in dry THF (10 mL), at
−78°C, under argon, was added a solution of methyl
diphenylphosphine oxide (2.16 g, 10 mmol) in dry THF
(10 mL). After stirring at −78°C for 30 min a solution of
PhTeBr (prepared in situ from bromine and diphenyl
ditelluride; 10 mmol) in dry THF (10 mL) was added.
The dark brownish color turned to pale-yellow immedi-
ately. The reaction mixture was stirred at −78°C for 1 h,
warmed up to −10°C for 1 h, then an aq sol. NH4C1 was
added and the mixture was extracted with. Ethyl acetate.
The organic layer was dried (MgSO4) and the solvent
removed. The residue was recrystallized from CH2Cl2/
Et2O (1:9); yellow powder mp: 123–124°C. 1H NMR (400
MHz, CDCl3) l 3.54 (d, 2H, J=7.44 Hz), 7.10–7.75 (m,
15H); 13C NMR (100 MHz, CDCl3): l 4.86 (d, JCP=67.6
Hz, CH2), 111.6, 127.8, 128.1, 128.2, 128.8, 130.5, 130.6,
131.4, 131.8, 132.8, 138.7. GC/MS m/z 422 (M++2), 291,
215, 201, 91 (100%).
25. General procedure for the preparation of vinylic tellurides
3: To a solution of phenyltelluroalkylphosphine oxide 2
(0.42 g; 1 mmol) in THF (5 mL) under argon at room
temperature was added the base (NaH for aromatic
aldehydes and ketones or t-BuOK for aliphatic alde-
hydes; 2 mmol). After 30 min of stirring, the appropriate
carbonyl compound (2 mmol) was added and stirring
continued by the time indicated in Table 1. The reaction
was stopped by adding water (10 mL) and extracted with
ethyl acetate. The organics were washed with water and
aq. NH4Cl, dried over MgSO4 and the solvent removed
under vacuum. The residue was purified by column chro-
matography over silica gel, eluting with hexane or hex-
ane/ethyl acetate. Selected spectroscopic data. Compound
3g: 1H NMR (200 MHz, CDCl3): l 1.55 (br s, 6H),
2.23–2.34 (m, 4H), 6.32 (s, 1H), 7.15–7.25 (m, 3H),
7.60–7.70 (m, 2H); 13C NMR (50 MHz, CDCl3): l 26.16,
26.97, 36.76, 38.46, 27.57, 93.65, 153.75, 114.62, 127.08,
129.18, 136.54; IR (film, cm−1) 2918, 1572, 1433, 1269;
GC/MS m/z 302 (M+), 207, 172, 129, 77 (100%). Anal.
calcd for C13H16Te: C, 52.07; H, 5.38. Found: C, 52.18;
12. Terao, J.; Kambe, N.; Sonoda, N. Tetrahedron Lett.
1996, 37, 4741–4744.
13. Kanda, T.; Sugiro, T.; Kambe, N.; Sonoda, N. Phospho-
rus Sulfur Silicon Relat. Elem. 1992, 67, 103–106.
14. Jang, W. B.; Oh, D. Y.; Lee, C. W. Tetrahedron Lett.
2000, 41, 5103–5106.
15. (a) Tucci, F. C.; Chieffi, A.; Comasseto, J. V.; Marino, J.
P. J. Org. Chem. 1996, 61, 4975–4984; (b) Comasseto, J.
V.; Berriel, J. Synth. Commun. 1990, 20, 1681–1685; (c)
Moraes, D. N.; Barrientos-Astigarraga, R. E.; Castelani,
P.; Comasseto, J. V. Tetrahedron 2000, 56, 3327–3337; (d)
Tucci, F. C.; Chieffi, A.; Comasseto, J. V. Tetrahedron
Lett. 1992, 33, 5721–5724; (e) Araujo, M. A.; Barrientos-
Astigarraga, R. E.; Ellensohn, R. M.; Comasseto, J. V.
Tetrahedron Lett. 1999, 40, 5115–5118; (f) Barrientos-
Astigarraga, R. E.; Moraes, D. N.; Comasseto, J. V.
Tetrahedron Lett. 1999, 40, 265–268.
16. Marino, J. P.; Tucci, F. C.; Comasseto, J. V. Synlett
1993, 761–763.
17. Araujo, M. A.; Comasseto, J. V. Synlett 1995, 1145–1148.
18. Huang, X.; Zhao, C. Q. Synth. Commun. 1997, 27, 237–
241.
19. (a) Chieffi, A.; Comasseto, J. V. Tetrahedron Lett. 1995,
35, 4063–4066; (b) Chieffi, A.; Comasseto, J. V. Synlett
1995, 671–674; (c) Huang, Y. Z.; Mo, X. S.; Wang, L.
Tetrahedron Lett. 1998, 39, 419–422.
20. Dabdoub, M. J.; Dabdoub, V. B.; Marino, J. P. Tetra-
hedron Lett. 2000, 41, 437–440 and 433–436.
1
H, 5.34. Compound 3h: H NMR (200 MHz, CDCl3): l
0.83 (s, 9H); 1.80–2.65 (m, 9H), 6.32 (s 1H); 7.10–7.25 (m,
3H), 7.55–7.75 (m, 2H); 13C NMR (50 MHz, CDCl3): l
27.60, 28.27, 29.09, 32.34, 36.61, 38.23, 47.79, 93.33,
114.55, 127.10, 129.18, 136.56, 153.69; IR (film, cm−1
)
2946, 1573, 1475, 1435, 1365, 1276; GC/MS m/z 356
(M+), 207, 129, 91, 57 (100%). Anal. calcd for C17H24Te:
C, 57.36, H, 6.80. Found: C, 56.68, H, 6.57. Compound
1
21. Silveira, C. C.; Perin, G.; Jacob, R. G.; Braga, A. L.
Phosphorus Sulfur and Silicon 2001, 172, 55–100.
22. (a) Silveira, C. C.; Perin, G.; Braga, A. L.; Dabdoub, M.
J.; Jacob, R. G. Tetrahedron 2001, 57, 5953–5959; (b)
Silveira, C. C.; Perin, G.; Braga, A. L.; Dabdoub, M. J.;
Jacob, R. G. Tetrahedron 1999, 55, 7421–7432; (c) Sil-
veira, C. C.; Perin, G.; Boeck, P.; Braga, A. L.; Petrag-
nani, N. J. Organomet. Chem. 1999, 584, 44–47; (d)
Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A. L.
3j: H NMR (200 MHz, CDCl3): l 7.16–7.39 (m, 14H),
7.74–7.79 (m, 2H); 13C NMR (50 MHz, CDCl3): l
108.75, 115.21, 127.11, 127.17, 127.9, 128.02, 128.14,
128.61, 128.67, 129.37, 137.97, 141.75, 142.80, 149.11; IR
(film, cm−1) 3055, 1573, 1492, 1437, 1264; GC/MS m/z
386 (M+), 256, 178 (100%). Anal. calcd for C20H16Te: C,
62.57; H, 4.20. Found: C, 62.32; H, 4.10.
26. Comasseto, J. V.; Petragnani, N. J. Organomet. Chem.
1978, 152, 295–304.