383-96-0Relevant academic research and scientific papers
Unsaturated nitrogen compounds containing fluorine. Part 13. Reaction of 2--1,1,1,3,3,3-hexafluoropropan-2-ide with compounds containing N=O or N-O bonds
Bell, David,Tipping, Anthony E.
, p. 279 - 286 (2007/10/02)
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 cycloaddition involving the N=O bonds, followed by elimination of hexafluoroacetone and niric 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-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--1-pyrazoline (21).This is confirmed by treatment of 1 with the oxadiazapentane 19.
Decomposition of perfluoro-(2,4,4,7,7,9-hexamethyl-3,8-dioxa-2,5,6,9-tetraazadec-5-ene) in the presence of fluoroalkenes, ethyne, benzene and nitroso compounds
Fisher, Raymond,Tipping, Antony E.
, p. 179 - 188 (2007/10/02)
Thermolysis of the azo compound (CF3)2NOC(CF3)2N=NC(CF3)2ON(CF3)2 (1) alone at 140 deg C gives nitrogen, hexafluoroacetone and the hydrazine (CF3)2NN(CF3)2 via (CF3)2N radical coupling in quantitative yield, while from decomposition in the presence of the alkenes CF2=CF2, CF2=CFCl and CF2=CHF (ca. 1:1 molar ratio) the major products are the dimer 2, trimer (CF3)2N(CF2CFCl)2CFClCF2N(CF3)2 and a mixture of tetramers (CF3)2N(C2HF3)4N(CF3)2, respectively.The (CF3)2N radicals generated from 1 can also be trapped with bromine (CF3)2NBr> and nitroso compounds (CF3)2NNRO (R=CF3 and Ph)>, but with ethyne or benzene near-quantitative yields of the amine (CF3)2NH are obtained.
PERFLUOROALKYL DERIVATIVES OF NITROGEN. PART LIII. REACTION OF PERFLUORO(2,5-DIMETHYL-4-OXA-3,5-DIAZAHEX-2-ENE) WITH FLUORO-OLEFINS
Fisher, R.,Haszeldine, R. N.,Tipping, A. E.
, p. 155 - 164 (2007/10/02)
Thermal decomposition of the title compound at 140 deg C gives mainly nitrogen, hexafluoroacetone and tetrakistrifluoromethylhydrazine while reaction with tetrafluoroethylene and chlorotrifluoroethylene affords equimolar mixtures of the 1:1 adducts (CF3)2C=NCF2CFXON(CF3)2 and (CF3)2C=NOCFXCF2N(CF3)2 (X=F and Cl) in highly yield via four-centre addition or a radical-cage process.
