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Synthesis 1986; 1986(10): 854-855
DOI: 10.1055/s-1986-31804
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Synthesis of Urazoles via Cycloaddition Employing 4-Phenyl-4H-1,2,4-Triazole-3,5-dione (PTAD) Transfer

Waldemar Adam* , Markus Dörr
  • *Institut für Organische Chemie, Universität Würzburg, Am Hubland D-8700 Würzburg, West Germany
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Publikationsdatum:
20. August 2002 (online)

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A new method was developed involving transfer of 4-phenyl-4H-1,2,4-triazole-3,5-dione (PTAD) from thermally labile urazoles 9 and 10 to bicyclic olefin derivatives 1-8, which irreversibly undergo cycloaddition accompanied by Wagner-Meerwein rearrangement. In most cases purer products and significantly improved yields of the corresponding urazoles 11-18 are obtained than by direct PTAD cycloaddition.