REACTION OF ACETYLENES WITH DIFLUORAMINE

The reaction of 3-hexyne with difluoramine, catalyzed by the boron trifluoride complex of phosphoric acid gave 3-hexanone, 3,3-bis(difluoramino)hexane, 3-difluoramino-3-fluorohexane, and N-(α-difluoraminopropyl)-propropionamide. Under the same conditions 1-hexyne gave 2-hexanone, 2,2-bis(difluoramino)hexane, 2-difluor-amino-2-fiuorohexane, and N-(difluoraminomethyl)valeramide. When sulfuric acid was used as the catalyst, 3-hexyne, 1-hexyne, and propargyl chloride were found to react with difluoramine to give 3,3-bis(difluoramino)-hexane, 2,2-bis(difluoramino)hexane, and1-chloro-2,2-bis(difluoramino)propane, respectively. Possible mechanisms are discussed. © 1968, American Chemical Society. All rights reserved.