348 J. Chin. Chem. Soc., Vol. 51, No. 2, 2004
Li et al.
Table 1. Synthesis of the Telluroesters
Entry
Ar
R1
R2
Time (h)
Yield (%)a
1
2
3
4
5
6
7
8
Ph
Ph
Ph
P-ClC6H4
o-BrC6H4
P-BrC6H4
P-BrC6H4
2
2
2
2
2
2
3
2
70
72
75
67
73
75
68
71
P-MeC6H4
Ph
Ph
Ph
P-MeC6H4
Ph
CH3
Ph
CH3CH2
a Isolated yields based on ditelluride.
dried over anhydrous Na2SO4. The solvent was removed un-
der reduced pressure; the residue was then purified by pre-
parative TLC on Silica gel with light petroleum and ethyl ace-
tate (100:1) as eluent to give the products.
7.70 (m).
617 p-BrC6H4COTeC6H4Me-p m.p.110-112 °C (lit.
111-112 °C); IR n (cm-1) 3100, 3080, 2980, 2880, 1670,
max
1595, 1580, 1530, 1490, 1385, 1250, 1200, 1170, 1070, 1010,
850, 780, 750, 680; 1H NMR 2.35 (3H, s), 6.90-7.20 (2H, m),
7.40-7.90 (6H, m).
In summary, a novel method for the preparation of
telluroesters has been provided. The advantages of which are
easily available and cheap materials, single product, simple
manipulation, and mild and neutral conditions.
716 CH3COTePh oil; IR n (cm-1) 3090, 3085, 2980,
max
1740, 1580, 1520, 1480, 1440, 1350, 1250, 1080, 1020, 1000,
760, 680; 1H NMR 2.40 (3H, s), 7.00-7.33 (3H, m), 7.51-7.80
(2H, m).
Scheme I
816 CH3CH2COTePh oil; IR n
(cm-1) 3080, 3075,
max
R1COCl
ArTeCOR1
ArTeCOR2
CeCl3/Sm
[ArTe-]
2985, 2960, 2890-2860, 1720, 1560, 1480, 1480, 1440, 1380,
1250, 1020, 1000, 740, 680; 1H NMR 1.16 (3H, t), 2.50 (2H,
q), 7.00-7.30 (3H, m), 7.40-7.73 (2H, m).
ArTeTeAr
(R2CO)2O
-
DATA OF THE PRODUCTS
ACKNOWLEDGEMENT
116 PhCOTePh m.p. 70-71 °C (lit. 71-72 °C); IR n
max
(cm-1) 3080, 3040, 1685, 1600, 1590, 1480, 1280, 1200,
The authors are grateful to the Natural Science Founda-
tion of Henan Province (Project No. 004030700) for financial
support.
1
1170, 1010, 1000, 850, 760, 740, 680, 650; H NMR 7.02-
8.03 (m).
217 PhCOTeC6H4Me-p m.p. 64-66 °C (lit. 65-67 °C); IR
n
max (cm-1) 3100, 3080, 2980, 2880, 1680, 1595, 1580, 1530,
Received May 23, 2003.
1490, 1385, 1250, 1200, 1170, 1070, 1010, 850, 780, 750,
690; 1H NMR 2.35 (3H, s), 6.90-7.10 (2H, m), 7.30-7.70 (5H,
m), 7.90-8.15 (2H, m).
32 p-ClC6H4COTePh m.p. 69-72 °C (lit. 71-72 °C); IR
REFERENCES
n
max (cm-1) 3080, 3050, 1690, 1600, 1580, 1490, 1440, 1250,
1200, 1160, 1085, 1010, 1000, 850, 780, 750, 680; 1H NMR
7.20-7.75 (m).
1. (a) Patai, S.; Rappoport, Z. The Chemistry of Organic
Seleium and Tellurium Compounds; John Wiley: Chichester,
1986, Vol. 1. (b) Schiesser, C. H.; Skidmore, M. A. J. Chem.
Soc., Perkin Trans. 1997, 1, 2689.
2. Sakaki, K.; Aso, Y.; Otsubo, T.; Ogura, F. Chem. Lett. 1986,
6, 977.
3. Chen, C.; Crich, D.; Papadatos, A. J. Am. Chem. Soc. 1992,
114, 8313.
4. Hiiro, T.; Morita, Y.; Inoue, T.; Kambe, N.; Ogawa, A.; Kyu,
416 o-BrC6H4COTePh m.p. 64-66 °C (lit. 65-67 °C); IR
max (cm-1) 3080, 3050, 1685, 1600, 1575, 1440, 1250, 1020,
n
850, 750, 680; 1H NMR 7.10-7.70 (m).
517 p-BrC6H4COTePh m.p. 76-78 °C (lit. 79 °C); IR
max (cm-1) 3100, 3080, 1690, 1595, 1580, 1530, 1490, 1250,
n
1200, 1170, 1070, 1010, 850, 780, 750, 680; 1H NMR 7.20-