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AN EFFECTIVE METHOD FOR THE SYNTHESIS OF 3,5-BIS(HALOMETHYL)-1,4-OXASELENANES AND THEIR DERIVATIVES

В. А. Потапов, М. В. Мусалов, Е. В. Абрамова, М. В. Мусалова, Ю. Ю. Русаков, С. В. Амосова
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Abstract


For the purpose of synthesis of selenium-containing heterocycil compounds, reactions of selenium dichloride and dibromide with diallyl ether were carried out and studied for the first time. I was found that the reaction of selenium dichloride proceeds regio- and stereoselectively and results in cis-3,5-bis(chloromethyl)-1,4-oxaselenane with 70% yield. In the case of selenium dibromide, 3,5-bis(bromomethyl)-1,4-oxaselenane is formed as a mixture of cis- and trans-diastereomers. From the obtained compounds, heretofore unknown 1,4-oxaselenane derivatives were synthesized: 3,5-bis(methoxymethyl)-, 4,4-dibromo-3,5-bis(chloromethyl)-, and 3,5-bis(bromomethyl)-4,4-dichloro-1,4-oxaselenanes. An example of unusually easy isomerization of 3,5-bis(halomethyl)-1,4-oxaselenane diastereomers was observed.

How to Cite
Potapov, V. A.; Musalov, M. V.; Abramova, E. V.; Musalova, M. V.; Rusakov, Yu. Yu.; Amosova, S. V. Chem. Heterocycl. Compd. 2014, 49, 1821. [Khim. Geterotsikl. Soedin. 2013, 1965.]

For this article in the English edition see DOI 10.1007/s10593-014-1435-1


Keywords


diallyl ether; diastereomers; selenium dibromide; selenium dichloride; 1,4-oxaselenane; seleniranium cation; anchimeric effect

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