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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1821–1826 | Cite as

An Effective Method for the Synthesis of 3,5-bis(halomethyl)-1,4-Oxaselenanes and their Derivatives

  • V. A. PotapovEmail author
  • M. V. Musalov
  • E. V. Abramova
  • M. V. Musalova
  • Yu. Yu. Rusakov
  • S. V. Amosova
Article

We report the first study of selenium dichloride and dibromide reactions with diallyl ether, aimed at the preparation of selenium-containing heterocyclic compounds. It was established that selenium dichloride reacted regio- and stereoselectively, giving cis-3,5-bis(chloromethyl)-1,4-oxaselenane in 70% yield. Selenium dibromide gave 3,5-bis(bromomethyl)-1,4-oxaselenane in 76% yield, as a mixture of cis and trans diastereomers. The obtained compounds were used for the synthesis of previously unknown 1,4-oxaselenanes: 3,5-bis(methoxymethyl)-, 4,4-dibromo-3,5-bis(chloromethyl)-, and 3,5-bis-(bromomethyl)-4,4-dichloro-1,4-oxaselenane. The diastereomers of 3,5-bis(halomethyl)-1,4-oxa-selenanes were found to undergo unusually facile isomerization.

Keywords

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

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. A. Potapov
    • 1
    Email author
  • M. V. Musalov
    • 1
  • E. V. Abramova
    • 1
  • M. V. Musalova
    • 1
  • Yu. Yu. Rusakov
    • 1
  • S. V. Amosova
    • 1
  1. 1.A. E. Favorsky Irkutsk Institute of ChemistrySiberian Branch of the Russian Academy of SciencesIrkutskRussia

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