Chemistry of Heterocyclic Compounds, Vol. 37, No. 6, 2001
EXAMPLE OF "DOUBLE"
ELIMINATION IN OXIDATION
OF A CYCLIC TELLURIDE
V. A. Potapov, S. V. Amosova, and I. V. Doron'kina
Keywords: divinyl sulfone, tellurenic acid, 1-thia-4-telluracyclohexane-1,1-dioxide, elimination.
The reaction of elimination of organyltellurenic acids, RTeOH, from organic telluroxides with
formation of olefins is well known [1-3]. On heating, cyclic tellurides undergo extrusion of the tellurium atom
with formation of a new carbon–carbon bond [4, 5].
We synthesized a series of cyclic tellurides earlier in [6-9]. While studying their chemical properties, we
observed a reaction of "double" elimination upon oxidation of 1-thia-4-telluracyclohexane-1,1-dioxide (1) [9].
Heating telluride 1 (145°C, 25 h) in the presence of air leads to divinyl sulfone in quantitative yield. When
heated under similar conditions under an argon atmosphere, telluride 1 is recovered unreacted. The reaction
probably occurs through oxidation of telluride 1 by the oxygen of air with formation of the intermediate
telluroxide 2 and subsequent elimination of tellurenic acid HTeOH.
O
O
O
O
O
O
S
S
S
O2
–[HTeOH]
Te
1
Te
O
2
1
13
Divinyl sulfone was identified with the help of H NMR and C using an authentic sample [10].
REFERENCES
1
.
T. Back, in: The Chemistry of Organic Selenium and Tellurium Compounds [S. Patai, ed.], Wiley, New
York (1987), Vol. 2, p. 91.
2
3
4
5
.
.
.
.
I. D. Sadekov, B. B. Rivkin, and V. I. Minkin, Usp. Khim., 56, 586 (1987).
N. Petragnani, Tellurium in Organic Synthesis, Academic Press, London (1994), p. 200.
E. Cuthbertson and D. D. MacNicol, Tetrahedron Lett., 1893 (1975).
E. Cuthbertson and D. D. MacNicol, J. Chem. Soc., Chem. Commun., 498 (1974).
_
_________________________________________________________________________________________
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences, Irkutsk
64033; e-mail: potapov@irioch.irk.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, p. 855,
6
June, 2001. Original article submitted April 15, 2001.
0009-3122/01/3706-0793$25.00©2001 Plenum Publishing Corporation
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