Unsaturated nitrogen compounds containing fluorine. Part 13 [1]. Reaction of 2-[5,5-dimethyl-3,3-bis(trifluoromethyl)-1-pyrazolin-1-ylio]-1,1,1,3,3,3-hexafluoropropan-2-ide with compounds containing N  O or N  O bonds [2]

Add time:08/02/2019    Source:sciencedirect.com

Reaction of the title azomethinimine (1) with nitrogen dioxide gives nitric oxide, hexafluoroacetone and 3,3-dimethyl-5,5-bis(trifluoromethyl)-1-pyrazoline (2) in high yield, while with the perfluoronitrosoalkanes RFNO (RF  CF3 and CF2CF2CF3) the products are hexafluoroacetone and the azimines 8a and 8b, respectively. The reactions involve initial [3 + 2] cycloaddition involving the N  O bonds, followed by elimination of hexafluoroacetone and nitric oxide to give 2 or of hexafluoroacetone to give 8. From reaction of 1 with nitrosyl chloride the major products are nitric oxide, 7-chloro-8,8,8-trifluoro-2-methyl-4,4,7-tris(trifluoromethyl)-5,6-diazaocta-1,5-diene (13) and 5,5-dimethyl-3,3-bis(trifluoromethyl)-1-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pyrazolidine (14) formed via decomposition of the 1:1 adduct containing C-chloro and N-nitroso substituents. The oxyl (CF3)2NO · attacks azomethinimine 1 at carbon and the resulting 1:1 adduct decomposes to give hexafluoroacetone, the pyrazoline 2 and (CF3)2N · radicals which are trapped by the oxyl to afford the oxadiazapentane (CF3)2NON(CF3)2 (19). Secondary reaction then takes place involving attack of the oxygen atom of the oxadiazapentane on 1 at carbon to give hexafluoroacetone, N,N-bis(trifluoromethyl)amine and 3-methyl-5,5 bis(trifluoromethyl)-3-[N,N-bis(trifiuoromethyl)methyl]-1-pyrazoline (21). This is confirmed by treatment of 1 with the oxadiazapentane 19.

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