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Synlett 2000; 2000(9): 1330-1332
DOI: 10.1055/s-2000-7129
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Intramolecular Iron(II)-Catalyzed Addition Reactions of Propargyloxycarbonyl Azides

Thorsten Bach* , Björn Schlummer, Klaus Harms
  • *Fachbereich Chemie der Philipps-Universität Marburg, 35032 Marburg, Germany; Fax +49(0)64 21/28 89 17; E-mail: bach@chemie.uni-marburg.de
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Publication Date:
31 December 2000 (online)

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The Fe(II)-catalyzed dediazotation of the propargyloxycarbonyl 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.

radical reactions - ring closure - catalysis - iron