Reactions of per(poly)-fluoroalkanesulfonyl azides with β-ketoester enamines, a new route to N-per(poly) fluoroalkanesulfonyl amidines

Per(poly)-fluoroalkanesulfonyl azides reacted readily with β-ketoester enamines to afford good yields of N-per(poly)-fluoroalkanesulfonyl amidines and diazoacetates. Similarly, treatment of the azides with the cyclo analogues ethyl 2-(1-morpholine) 1-cyclopentenecarboxylate gave amidines containing diazo groups. The reaction mechanisms and solvent effects are discussed.