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Convenient Room‐Temperature, Mercury‐Assisted Synthesis of Tetrazoles by 1,3‐Dipolar Cycloaddition
Author(s) -
Klapötke Thomas M.,
Krumm Burkhard,
Moll Richard
Publication year - 2011
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201001046
Subject(s) - chemistry , cycloaddition , tetrazole , organomercury , organomercury compounds , moiety , regioselectivity , nuclear magnetic resonance spectroscopy , raman spectroscopy , 1,3 dipolar cycloaddition , mercury (programming language) , azide , catalysis , single crystal , crystallography , stereochemistry , organic chemistry , analytical chemistry (journal) , metal , physics , optics , computer science , programming language
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.