Reaction of 2,6-Bis(4-azidobenzylidene)-4-methyl-cyclohexanone with Organophosphorus Reagents. Synthesis of Some Benzylidene-1, 2, 3-triazole Derivatives


TRIPHENYLPHOSPHINE (1) reacts with 2,6-bis(4-azido-benzylidene)-4-methylcyclohexanone (4) to give the respective triphenylphosphinylidenetriaz-1-enyl (5a) and triphenylphosphinylidene- amino (5b). Moreover, reaction of aryl azide (4) with trisdimethy-laminophosphine (2) in refluxing toluene afforded the new products (6a, b). On the other hand, phosphorus ylides (3a-d) react with azidobenz-ylidene (4) to give the corresponding 1,5-disubstituted-1,2,3-triazoles (7a-d) and triphenylphosphine oxide. Possible reaction mechanisms are considered and the structural assignments are based on compatible analytical and spectroscopic results.