4818
P. Arsenyan et al. / Tetrahedron Letters 43 (2002) 4817–4819
Table 1. 2,5-Diarylselenophenes from thermal decomposition of selenadiazoles 1 and 2 in the presence of arylacetylenes
1b and 2b react with a second molecule of the aryl-
acetylene to yield the corresponding 2,5-diarylse-
lenophenes (3–5) and 1,4-diarylbutadi-1,3-ynes (6–8).
The yields of selenophenes 3–5 are presented in Table 1.
As can been seen from the results presented, the appli-
cation of 4-phenyl-1,2,3-selenadiazole 1 for the synthe-
sis of 2,5-diarylselenophenes is preferable to the use of
the thienyl analogue 2. In this case 4-phenylselenadia-
zole 1 serves as the source of selenium for the forma-
tion of 2,5-diphenylselenophenes 3–5 in contrast to the
tributylstannyl radical-catalyzed decomposition of 4-
phenylselenadiazole in the presence of olefins giving
phenylacetylene.5
II: A Review of the Literature 1982–1995; 1996, Storr, R.
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Our attempts to prepare 2,5-bis(trimethylsilyl)- and 2,5-
bis(tert-butyl)selenophenes from 1 and 2 with an excess
of trimethylsilylacetylene and 3,3-dimethylbut-1-yne
failed. Only 2,5-diphenyl- or 2,5-di(2-thienyl)seleno-
phenes were obtained as products of selenadiazole
decomposition.
In summary, we have developed a simple method for
the preparation of 2,5-diarylselenophenes from 4-
phenyl- and 4-(2-thienyl)-1,2,3-selenadiazoles.
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Acknowledgements
6. Lalezari, I.; Shafiee, A.; Yalpani, M. Tetrahedron Lett.
Financial support from the Latvian Council of Science
(grant Nos. 187 and 189) is gratefully acknowledged.
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