Study on the reactions of fluoroalkanesulfonyl azides with cycloalkenyl ether and aryl ynamines

The reactions of fluoroalkanesulfonyl azides with some electron-rich compounds have been studied in detail. Cycloalkenyl vinyl ethers reacted with readily at 0 °C to give the corresponding ring-contraction N-fluoroalkanesulfonyl amidine analogues . In contrast, aryl ynamine generated in situ reacted with affording fluorinated α-diazoamidines , which were decomposed slowly at room temperature to form [1-diethylamino-2-(4-nitro-phenyl)-2-oxo-eth-(Z)-ylidene]-fluoroalkanesulfinyl imine with elimination of nitrogen gas. Possible mechanisms for these reactions were proposed.