Preparation and X-ray crystal structures of two aliphatic selenenyl bromides stabilized by N-Se coordination

Thomas G. Back, Ziad Moussa, Masood Parvez

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

(1R)-2-endo-(Dimethylamino)methyl-2-exo-methoxy-3-endo-camphorylselenenyl bromide and its 2-endo-(pyrrolidenyl)methyl analogue were prepared from (1R)-2-endo-acetamidomethyl-2-exo-hydroxy-3-endo-camphoryl diselenide. Both compounds showed an unusual lack of reactivity in electrophilic oxyselenenylation and cyclization reactions that are typical of other selenenyl bromides. X-ray crystallography indicated that both compounds have strong N - Se interactions, with N - Se interatomic distances of ca. 2.1 Å, which diminish the electrophilic character of the selenium atom.

Original languageEnglish
Pages (from-to)2569-2579
Number of pages11
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume179
Issue number12
DOIs
Publication statusPublished - Dec 2004
Externally publishedYes

Keywords

  • Electrophiles
  • N - Se coordination
  • Selenenyl bromides
  • X-ray structures

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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