Convenient Room-Temperature, Mercury-Assisted Synthesis of Tetrazoles by 1,3-Dipolar Cycloaddition

✍ Scribed by Thomas M. Klapötke; Burkhard Krumm; Richard Moll

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 373 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-1948
• DOI: 10.1002/ejic.201001046

✦ Synopsis

Abstract

The intermolecular 1,3‐dipolar cycloaddition of organomercury(II) azides R^1^HgN~3~ (R^1^ = Me, Ph) to organonitriles R^2^CN (R^2^ = Me, Ph, C~6~F~5~) forms organomercury(II) tetrazoles R^1^Hg(N~4~C)R^2^ [R^1^ = Me, R^2^ = Me (1); R^1^ = Me, R^2^ = Ph (2); R^1^ = Ph, R^2^ = Me (3); R^1^ = Ph, R^2^ = Ph (4); R^1^ = Ph, R^2^ = C~6~F~5~ (5)]. The reaction is a direct and regioselective formation of the tetrazole moiety, which is easily performed at room temperature or slightly elevated temperature without a catalyst and furnishes quantitatively the pure product. In addition to characterization by multinuclear NMR spectroscopy, IR and Raman spectroscopy, as well as mass spectrometry, the mercury content was determined. Furthermore, X‐ray diffraction studies were performed, and the crystal structures for 1–3 and 5 are reported.