Replacement of two methylseleno groups by two phenylthio groups in the thermal reaction of 1,2-bis(methylseleno)-1-phenylethene with diphenyl disulfide

Full text of DOI:10.1023/A:1021676418243

Russian Journal of Organic Chemistry, Vol. 38, No. 9, 2002, p. 1374. Translated from Zhurnal Organicheskoi Khimii, Vol. 38, No. 9, 2002, p. 1426.
Original Russian Text Copyright
2002 by Potapov, Amosova, Belozerova, Gendin.
SHORT
COMMUNICATIONS
Replacement of Two Methylseleno Groups by Two Phenylthio
Groups in the Thermal Reaction of 1,2-Bis(methylseleno)-
1-phenylethene with Diphenyl Disulfide
V. A. Potapov, S. V. Amosova, O. V. Belozerova, and D. V. Gendin
Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: potapov@irioch.irk.ru
Irkutsk State Technical University, Irkutsk, Russia
Received June 10, 2002
We have revealed a surprisingly facile replacement
of two methylseleno groups by two phenylthio groups
in the thermal reaction of 1,2-bis(methylseleno)-1-
phenylethene (I) with diphenyl disulfide. Heating of
bis(methylseleno)ethene (I) (Z/E isomer ratio 2:3)
with diphenyl disulfide in a sealed ampule (150 C,
120 h) leads to formation of 1-phenyl-1,2-bis(phenyl-
thio)ethene (II) (Z/E isomer ratio 1:2) in 40% yield
(the yield was calculated on the initial amount of
ethene I and was not optimized) and methylseleno
phenyl sulfide (yield 42%). Presumably, the reaction
follows a radical mechanism involving homolytic
dissociation of the carbon selenium bond and sub-
sequent reaction of the vinyl radical thus formed
with diphenyl disulfide. We are now studying the
possibility of extending this reaction to other organo-
selenium compounds.
1,2-Bis(methylseleno)-1-phenylethene (I) was
synthesized by addition of dimethyl diselenide to
phenylacetylene according to the procedure reported
in [1]. The spectral parameters and physical constants
of 1,2-bis(phenylthio)-1-phenylethene (II) were in
agreement with published data [2].
REFERENCES
1. Potapov, V.A., Amosova, S.V., Starkova, A.A.,
Zhnikin, A.R., Doron’kina, I.V., Beletskaya, I.P.,
and Hevesi, L., Sulfur Lett., 2000, vol. 23, no. 5,
pp. 229 238.
2. Kuniyasu, H., Ogawa, A., Miyazaki, S.-I., Ryu, I.,
Kambe, N., and Sonoda, N., J. Am. Chem. Soc., 1991,
vol. 113, no. 26, pp. 9796 9803.
1070-4280/02/3809-1374$27.00 2002 MAIK Nauka/Interperiodica