Intramolecular iron(II)-catalyzed addition reactions of propargyloxycarbonyl azides

T. Bach, B. Schlummer, K. Harms

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

The Fe(II)-catalyzed dediazotation of the propargyl-oxycarbonyl azides 2-4 was studied. In the case of phenyl- (2) and n-butyl-substituted (3) alkynes the products 5 and 6 of an intramolecular syn-aminochlorination were isolated in excellent yields (81-99%). The t-butyl-substituted substrates 4 yielded the 4-alkylidene-5-alkoxyoxazolidinones 7-9 (91-99%) which did not contain a chlorine atom. Their formation is explained by a consecutive ionic reaction which occurs after the cyclization.

Original languageEnglish
Pages (from-to)1330-1332
Number of pages3
JournalSynlett
Issue number9
StatePublished - 2000

Keywords

  • Catalysis
  • Iron
  • Radical reactions
  • Ring closure

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