AN EFFECTIVE METHOD FOR THE SYNTHESIS OF 3,5-BIS(HALOMETHYL)-1,4-OXASELENANES AND THEIR DERIVATIVES
DOI:
https://doi.org/10.1007/1020Keywords:
diallyl ether, diastereomers, selenium dibromide, selenium dichloride, 1, 4-oxaselenane, seleniranium cation, anchimeric effectAbstract
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
