Preparation, Structure, and Reactivity of 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene, a New Stable Carbene

Authors

  • Prof. Dr. Dieter Enders,

    Corresponding author
    1. Institut für Organische Chemie der Technischen Hochschule Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany) Telefax: Int. code + (241)8888-127
    • Institut für Organische Chemie der Technischen Hochschule Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany) Telefax: Int. code + (241)8888-127
    Search for more papers by this author
  • Dipl.-Chem. Klaus Breuer,

    1. Institut für Organische Chemie der Technischen Hochschule Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany) Telefax: Int. code + (241)8888-127
    Search for more papers by this author
  • Dr. Gerhard Raabe,

    1. Institut für Organische Chemie der Technischen Hochschule Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany) Telefax: Int. code + (241)8888-127
    Search for more papers by this author
  • Dr. Jan Runsink,

    1. Institut für Organische Chemie der Technischen Hochschule Professor-Pirlet-Strasse 1, D-52074 Aachen (Germany) Telefax: Int. code + (241)8888-127
    Search for more papers by this author
  • Dr. J. Henrique Teles,

    Corresponding author
    1. BASF AG, Ammoniaklaboratorium D-67056 Ludwigshafen (Germany) Telefax: Int. code + (621)60-56116
    • BASF AG, Ammoniaklaboratorium D-67056 Ludwigshafen (Germany) Telefax: Int. code + (621)60-56116
    Search for more papers by this author
  • Dr. Johann-Peter Melder,

    1. BASF AG, Ammoniaklaboratorium D-67056 Ludwigshafen (Germany) Telefax: Int. code + (621)60-56116
    Search for more papers by this author
  • Dr. Klaus Ebel,

    1. BASF AG, Ammoniaklaboratorium D-67056 Ludwigshafen (Germany) Telefax: Int. code + (621)60-56116
    Search for more papers by this author
  • Dr. Stefan Brode

    1. BASF AG, Ammoniaklaboratorium D-67056 Ludwigshafen (Germany) Telefax: Int. code + (621)60-56116
    Search for more papers by this author

  • This work was supported by the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (SFB 380, Leibniz-Preis). We are obliged to Dr. Nigel Walker, BASF AG, for the X-ray structure determination of 3.

Abstract

original image

Stable to 150 °C, the heterocyclic carbene 1 is characterized by the typical reactivity of a nucleophilic carbene. Dihydrotriazole 1 can be prepared by simple thermal decomposition of its methanol adduct. X-ray crystal structure analysis, ab initio calculations, and reactivity studies confirm the nucleophilic carbene character of 1.

Ancillary