REACTIONS OF CHLORO OLEFINS WITH DIFLUORAMINE

The reaction of 2-chloro-2-penten-4-one with difluoramine and fuming sulfuric acid gave 2,2,4,4-tetrakis-(difluoramino)pentane, 2-chloro-2,4,4-tris(difluoramino)pentane, and 2-chloro-3,4,4-tris(difluoramino)pentane. cis-3-Chlorocrotonic acid gave 3-chloro-3-(difluoramino)butyric acid but ethyl 3-chlorocrotonate did not react. 1,1-Dichloro-1-buten-3-one gave 1,1-dichloro-3,3-bis(difluoramino)-1-butene when a very large excess of difluoramine was used and N-[2,2-dichloro-1,2-bis(difluoramino)ethyl]acetamide with less difluoramine. A possible mechanism for the formation of the latter compound is presented. The reaction of 1,1-dichloroethylene with difluoramine and fuming sulfuric acid gave 1,1-dichloro-1-(difluoramino)ethane and 1-chloro-1,1-bis(difluoramino)ethane. © 1969, American Chemical Society. All rights reserved.