Abstract
AbstractThe 1‐adamantyl substituted stable carbene 5 and the biscarbene 9 of the 1,2,4‐triazole series with sterically shielding groups at the position 4 of the heterocyclic ring (dbmp, dipp) have been synthesized in three steps starting from the derivatives of 1,3,4‐oxadiazole 1,6. A new method for the preparation of 1,3,4‐triaryl‐1,2,4‐triazol‐5‐ylidenes (14 a‐c) has also been proposed and includes the Vilsmeier reaction of 2‐benzoyl‐1‐formylphenylhydrazine with phosphorus chloroxide and aromatic amines, followed by deprotonation of the obtained 1,3,4‐triaryl‐1,2,4‐triazolium salts. The method allows introduction of steric shielding substituents to the 4‐position of the heterocycle. The resulting carbenes show promise as nucleophilic catalysts and ligands for carbene complex catalysts of organic reactions.
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