2
91
SELENOPHENE SYNTHESIS IN THERMAL REACTIONS
At 440 (for Et Se) and 490°C (for Me Se) reaction
3) becomes negligible, and due to reversibility of reac-
tion (1) the selectivity of selenophene formation along
reaction (2) considerably increases compared to the pro-
cess performed without methanol.
flow of acetylene (flow rate 3 l/h) was charged a mixture
of 14.7 g (107 mmol) of diethyl selenide and 0.63 g
(20 mmol) of methanol at a rate 10 ml/h for 77 min. At
the output of the reactor was collected 13.76 g of con-
densate containing according to GLC 13.43 g of
selenophene (yield 89.5%).
2
2
(
The synthesis was carried out in quartz tubular reac-
tor flushed with nitrogen prior to the experiment. It was
heated to the required temperature specified above (heat-
ing zone 30´650 mm). Into the heated reactor was charged
in an acetylene flow a mixture of Me Se (or Et Se) with
REFERENCES
1. Magdesieva, N.N., Adv. Heterocycl. Chem., 1970, vol. 12,
p. 1.
2
2
2.
Korchevin, N.A., Ostroukhova, L.A., Sukhomazova, E.N.,
Zhnikin,A.R., Deryagina, E.N., and Voronkov, M.G., Khim.
Geterotsikl. Soed., 1987, p. 279.
methanol at the molar ratio selenideacetylene 1:2. At
the output of the reactor the products were collected in a
cooled trap (20°C) and were analyzed by GLC on a
chromatograph LKhM-80MD at linear programming of
oven temperature. The stationary phase used was silicon
XE-60, 5% on Chromaton N-AW-HMDS, carrier gas
helium, column 2000´3 mm.
Selenophene synthesis from diethyl selenide and
acetylene in the presence of 20 mol% of methanol.
Into the above described reactor heated to 440°C in a
3. Deryagina, E.N., Sukhomazova, E.N., Levanova, E.P., and
Voronkov, M.G., Zh. Obshch. Khim., 1996, vol. 66, p. 1051.
4.
Deryagina, E.N., Sukhomazova, E.N., Bannikova, O.B., and
Voronkov, M.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1979,
p. 2103.
5
. Yagupolskii, D.P., Elementarnye reaktsii i mekhanizm
piroliza uglevodorodov (Elementary Reactions and
Mechanism of Hydrocarbons Pyrolysis), Moscow: Khimiya,
1990, p. 213.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 2 2004