Reaction of SeOCF3 and SeO2CF3 groups with π-electron systems in ground and excited states

The dipole moments and ultraviolet spectra were measured for selenium compounds containing SeOCF₃ and SeO₂CF₃ groups. It is shown that in the ground state the SeO₂CF₃ group has a greater tendency toward conjugation with the -electron system of the benzene ring thandoes the SeOCF₃ group. In the ground state, selenium compounds containing SeOCF₃ and SeO₂CF₃ groups have a smaller conjugation effect than corresponding sulfur compounds. Oxidation of SeCF₃ to SeOCF₃ decreases the degree to which the uncollectivized electrons of selenium take part in conjugation with electron-accepting groups. In the unexcited state the free electrons of selenium in SeCH₃ and SeCF₃ groups are more mobile than those of sulfur in SCH₃ and SCF₃ groups, and the * level of the Se=O groups is lower than that of the S=O group.     

Trifluormethylselenyl-Verbindungen des N,P und As

Trifluoromethylselenyl Compounds of N, P, and As The reaction of CF₃SeBr with NH₃ leads, depending on conditions, to (CF₃Se)_nNH_3?n, where n = 1, 2 or 3. CF₃SNCO reacts with CF₃SeNH₂ to give CF₃SNHCONHSeCF₃, and (CF₃Se)₃N with P(C₆H₅)₃ provides CF₃SeN ?P(C₆H₅)₃. (CF₃Se)₃E (where E = P, As) is formed by the reaction of Hg(SeCF₃)₂ with EBr₃ in CS₂. Analogously, from Hg(SeCF₃)₂ and P₂J₄ in CS₂ (CF₃Se)₂PP(SeCF₃)₂ is obtained that contains (CF₃Se)₃P as a contamination. While reacting C₆H₅PJ₂ or C₆H₅P(J)(J)C₆H₅ with Hg(seCF₃)₂ respectiverly C₆H₅P(SeCF₃)₂ is formed. The latter can be also obtained from (C₆H₅P)₅ and CF₃SeSeCF₃. IR, ¹⁹F, ³¹P, ⁷⁷Se NMR, and MS data are given.     

Recent Progress Toward Trifluoromethylselenolation Reactions

Recently, a great deal of work has been done in the construction of C–CF₃ or C–SCF₃ bonds, because these fluorine groups display remarkable biological properties. Despite a trifluoromethylseleno group like CF₃ or SCF₃ may also have potential biological activity, the work on the construction of the C–SeCF₃ bond is rarely reported. This mini‐review highlights recent developments in trifluoromethylselenolation reactions using fluorine reagents, such as (Me₄N )SeCF₃ , ClSeCF₃ , [(bpy)Cu(SeCF₃ )]₂, Me₃SiCF₃ , and HCF₃ . Five approaches to the trifluoromethylselenolation of organic compounds are summarized: (1) trifluoromethylselenolation of aryl, alkyl, and heteroaryl halides, aromatic compounds, and boronic acids; (2) trifluoromethylselenolation of terminal alkynes and propargylic chlorides; (3) trifluoromethylselenolation of allylic bromides, vinyl halides, α‐bromo‐α,β‐unsaturated carbonyl compounds, and acyl chlorides; (4) trifluoromethylselenolation of diazo compounds; and (5) synthesis of trifluoromethyl selenides from selenocyanates and fluoroform.     

Perfluormethyl-element-liganden XII. Zweikernkomplexe des rheniums: Re2(CO)8XY [1]

The reaction of Re₂(CO)₁₀ with E₂(CF₃)₄ (E = P, As) yields the binuclear complexes Re₂(CO)₈[E(CF₃)₂]₂ with two E(CF₃)₂ bridges. The complexes Re₂(CO)₈E(CF₃)₂I (E = P, As) and Re₂(CO)₈As(CF₃)₂Cl, containing two different bridges, are formed in the reactions of Re₂(CO)₁₀ with (CF₃)₂EI (E = P, As) and (CF₃)₂AsCl, respectively. A series of new binuclear complexes is obtained on substitution of iodine in the compounds Re₂(CO)₈E(CF₃)₂I (E = P, As) by SCH₃, SCF₃, SeCF₃, P(CH₃)₂ and H. The binuclear complexes Re₂(CO)₈(E′CF₃)₂ having two E′CF₃ bridges (E′ = S, Se) are obtained reacting Re(CO)₅I With Hg(E′CF₃)₂. At room temperature the mononuclear complex Re(CO)₅SeCF₃ is obtained. Substitution of iodine in Re₂(CO)₈I₂ by SCF₃ also yields the symmetrical compound Re₂(CO)₈(SCF₃)₂; reduction with NaBH₄ gives the binuclear hydride Re₂(CO)₈HJ. - IR and NMR spectra (¹H, ¹⁹F) of the new complexes are reported and discussed.     

Darstellung und Reaktionen von Selenocarbonyldifluorid und seines cyclischen Dimeren 2,2,4,4-Tetrafluor-1,3-diselenetan [l]

Inhaltsübersicht. Das erstmals hergestellte B(SeCF₃)₃ zerfällt unter dem katalytischen Einfluß von Alkalifluoriden zu F₂C=Se und BF₃. In Anwesenheit von BF₃ polymerisiert F₂CSe bereits. bei ?;80°C. Oberhalb 150°C depolymerisiert (F₂CSe)_n wieder zu F₂C=Se und. Durch Halogenaddition an F₂C = Se gewinnt man F₂XCSeX (X = Cl, Br). Das in der Reihe Cl_3–nF_nCSeCl noch fehlende Cl₂FCSeCl wird durch Umsetzung von CSe₂, ClF und Cl₂ synthetisiert. F_nCl_3–nCSeCl (n = 1. 2) liefert mit Zinn die entsprechenden symmetrischen Diselane, mit AgCN die Selenocyanate. Durch Halogenaustausch mit BX₃ (X = Cl, Br) wird umgewandelt. XC(S)Cl reagiert mit Hg(SeCF₃)₂ zu CF₃SeC(S)X (X = F, Cl. CF₃Se). Daraus werden durch Chloraddition die entsprechenden Sulfenylchloride synthetisiert. IR-NMR- und Massenspektren der neu hergestellten Substanzen werden angegeben. Preparation and Reactions of SeCF₂ and its Cyclic Dimer 2,2,4,4-Tetrafluoro-1,3-diselenetane Abstract. B(SeCF₃)₃, prepared for the first time, decomposes under the influence of alkali metal fluorides to F₂C=Se and BF₃. In presence of BF₃, SeCF₂ polymerizes even at ?80°C. Above 150°C (F₂CSe)n depolymerizes to F₂C = Se and Halogen addition to F₂C=Se produces F₂XCSeX (X = Cl, Br). The compound Cl₂FCSeCl could be synthesized by the reaction of CSe₂ with ClF and Cl₂. These selenenylchlorides react with tin producing the corresponding symmetric diselenides whereas with AgCN the selenocyanates are formed. can be transformed to through halogen exchange reaction with BX₃ (X = Cl, Br). XC(S)Cl reacts with Hg(SeCF₃)₂ to give CF₃SeC(S)X (X = F, Cl. CF₃Se), from which the corresponding sulfenylchlorides can be synthesized by chlorine addition. I.r., n.m.r., and mass spectra of the newly prepared compounds are reported.     

Perfluormethyl-Element-Liganden. Reaktionen der Metallhydride π-C5H5(CO)3 MH (M = Cr,Mo, W) mit Organoelement-Elementverbindungen des Typs R2EER2 und RE′ E′ R (E = As; E′ = S,Se; R = CH3 CF3)

Perfluoromethyl Element Ligands. XXX. Reactions of the Metal Hydridesπ-C₅H₅(CO)₃MH (M = Cr, Mo, W) with Organoelement-Element Compounds of the Type R₂ EER₂ and RE′ ′E ′R (E = P, As; E′ = S, Se; R = CH₃, CF₃) Cleavage reactions of R₂EER₂ and RE′E′R, respectively, (E = P, As; E′ = S, Se; R = CH₃, CF₃) with complexes π-C₅H₅(CO)₃MH (M = Cr, Mo, W) are used (a) to prepare known and novel complex subsituted phosphanes, arsanes, sulfanes, or selanes π-C₅H₅(CO)₃MER₂ (I) and π-C₅H₅(CO)₃ME′R (II), respectively, (b) to study the reactivity trends as a function of E, E′, R, and M (see Inhaltsübersicht). The tendency observed for the formation of the binuclear complexes [π-C₅H₅(CO)₂MER₂]₂ and [π-C₅H₅(CO)₂ME′R]₂, respectively, in following reactions of I and II increases in the series W ? Mo ≤ Cr and SeCF₃ < As(CF₃)₂ < SCF₃ ≈ P(CF₃)₂ < SeMe < AsMe₂ ?; PMe₂ ≈ SMe.     

Physikalische und spektroskopische daten von trifluormethylselenol und derivaten

The characterization of the compounds CF₃SeX (X = H, Cl, Br, CN, CF₃, SeCF₃) is completed by the report of melting points, boiling points, enthalpies of vaporization and entropies of vaporization. Ultraviolet and mass spectra are presented and discussed. An improved synthesis for CF₃SeH is reported.     

Trifluoromethylselenate(0), [SeCF3]—, and Trifluoromethyltellurate(0), [TeCF3]— — Crystalline Products of the Reduction of the Bis(trifluoromethyl)dichalkogen Compounds,E2(CF3)2 (E = Se,Te), with Tetrakis(dimethylamino)ethene (TDAE)

[Bis(dimethylamino)ethanediylidene]bis(dimethylammonium) bis(trifluoromethylchalcogenates(0)), (TDAE)[ECF₃]₂ (E = Se, Te), are quantitatively formed from the reductions of E₂(CF₃)₂ with tetrakis(dimethylamino)ethene, TDAE. Both compounds are bright yellow to orange solids which crystallize isostructurally with the corresponding sulfur derivative in the orthorhombic space group Pbca (No. 61). (TDAE)[SeCF₃]₂ has alternatively been prepared by cation exchange from [NMe₄]SeCF₃ and (TDAE)Br₂.     

Synthesis and repellent properties of vinylidene fluoride-containing polyacrylates

Fluorinated polyacrylats with side group containing vinylidene fluoride (VDF) units (CF₃(CF₂)_n (CH₂CF₂)_m, n = 3, 5; m = 1, 2) were successfully synthesized. The water and oil repellency properties of these polymers are similar to those of fluorinated polyacrylate with side group containing long perfluorooctyl group (CF₃(CF₂)₇). The thermal telomerization of CF₃(CF₂)₅I and CF₃(CF₂)₃I with vinylidene fluoride (VDF) provided CF₃(CF₂)₅CH₂CF₂I (1b) and CF₃(CF₂)₃CH₂CF₂CH₂CF₂I (1c), respectively. The addition of 1b with ethylene followed by hydrolysis gave CF₃(CF₂)₅CH₂CF₂CH₂CH₂OH (2b). Treatment of 1c with ethyl vinyl ether in the presence of Na₂S₂O₄ followed by reduction produced CF₃(CF₂)₃CH₂CF₂CH₂CF₂CH₂CH₂OH (2c). Fluoroacrylates 3b-d were prepared by acrylation of the corresponding fluoroalcohols 2b-d. The semi-continuous process emulsion co-polymerization of 3a-d with octadecyl acrylate and 2-hydroxylethyl acrylate initiated by (NH₄)₂S₂O₈ in the presence of a mixture emulsifiers of polyoxyethylene(10)nonyl phenyl ether (TX-10) and sodium lauryl sulfate provided stable latexes 4a-d, respectively. The water and oil repellency properties of 4b (R_f: CF₃(CF₂)₅CH₂CF₂) and 4c (R_f: CF₃(CF₂)₃CH₂CF₂CH₂CF₂) containing vinylidene fluoride (VDF) units were similar to those of 4a (R_f: CF₃(CF₂)₇) containing long perfluoroalkyl group and much better than those of polymer 4d (R_f: CF₃(CF₂)₃) with short perfluoroalkyl chain. Thus, polyacrylates containing vinylidene fluoride units showed promising aspects as the alternatives to the currently used water and oil repellent agents with long perfluoroalkyl chains.     

1,1,1,3,3,-pentafluorobutane (HFC-365mfc): atmospheric degradation and contribution to radiative forcing

The rate constant for the reaction of the hydroxyl radical with 1,1,1,3,3-pentafluorobutane (HFC-365mfc) has been determined over the temperature range 278–323K using a relative rate technique. The results provide a value of k(OH+CF₃CH₂CF₂CH₃)=2.0×10⁻¹²exp(−1750±400/T) cm³ molecule⁻¹ s⁻¹ based on k(OH+CH₃CCl₃)=1.8×10⁻¹² exp (−1550±150/T) cm³ molecule⁻¹ s⁻¹ for the rate constant of the reference reaction. Assuming the major atmospheric removal process is via reaction with OH in the troposphere, the rate constant data from this work gives an estimate of 10.8 years for the tropospheric lifetime of HFC-365mfc. The overall atmospheric lifetime obtained by taking into account a minor contribution from degradation in the stratosphere, is estimated to be 10.2 years. The rate constant for the reaction of Cl atoms with 1,1,1,3,3-pentafluorobutane was also determined at 298±2 K using the relative rate method, k(Cl+CF₃CH₂CF₂CH₃)=(1.1±0.3)×10⁻¹⁵ cm³ molecule⁻¹ s⁻¹. The chlorine initiated photooxidation of CF₃CH₂CF₂CH₃ was investigated from 273–330 K and as a function of O₂ pressure at 1 atmosphere total pressure using Fourier transform infrared spectroscopy. Under all conditions the major carbon-containing products were CF₂O and CO₂, with smaller amounts of CF₃O₃CF₃. In order to ascertain the relative importance of hydrogen abstraction from the (SINGLE BOND)CH₂(SINGLE BOND) and (SINGLE BOND)CH₃ groups in CF₃CH₂CF₂CH₃, rate constants for the reaction of OH radicals and Cl atoms with the structurally similar compounds CF₃CH₂CCl₂F and CF₃CH₂CF₃ were also determined at 298 K k(OH+CF₃CH₂CCl₂F)=(8±3)×10⁻¹⁶ cm³ molecule⁻¹ s⁻¹; k(OH+CF₃CH₂CF₃)=(3.5±1.5)×10⁻¹⁶ cm³ molecule⁻¹ s⁻¹; k(Cl+CF₃CH₂CCl₂F)=(3.5±1.5)×10⁻¹⁷ cm³ molecule⁻¹ s⁻¹]; k(Cl+CF₃CH₂CF₃)<1×10⁻¹⁷ cm³ molecule⁻¹ s⁻¹. The results indicate that the most probable site for H-atom abstraction from CF₃CH₂CF₂CH₃ is the methyl group and that the formation of carbonyl compounds containing more than a single carbon atom will be negligible under atmospheric conditions, carbonyl difluoride and carbon dioxide being the main degradation products. Finally, accurate infrared absorption cross-sections have been measured for CF₃CH₂CF₂CH₃, and jointly used with the calculated overall atmospheric lifetime of 10.2 years, in the NCAR chemical-radiative model, to determine the radiative forcing of climate by this CFC alternative. The steady-state Halocarbon Global Warming Potential, relative to CFC-11, is 0.17. The Global Warming Potentials relative to CO₂ are found to be 2210, 790, and 250, for integration time-horizons of 20, 100, and 500 years, respectively. © 1997 John Wiley & Sons, Inc.     

Synthése d'époxydes et d'éthers glycidiques á chaîne chlorofluorée

Epoxides of general formula

(II, V) (R_F,Cl = Cl ; CF₃ ; Cl(CFClCF₂)_n?) are prepared from chlorohydrines R_F,ClCCl₂CH₂CHClCH₂OH (I).These chlorhydrines are monoadducts of carbon tetrachloride 1,1,1 trichlorotrifluoroethane, telomers Cl(CFClCF₂)_nCCl₃, with allyl alcohol.Reactions of these epoxides with lithium aluminium hydride and/or sulfuric acid lead to corresponding secondary alcohols and/or diols. Glycidyl ethers of (I) and (II,n) with epichlorhydrin could not be obtained. However, epichlorhydrin reacts with the more acidic chlorofluorinated alcohol CFCl₂CF₂CH₂OH. Thus, the glycidyl ether

is prepared.     

β-Functionalized ethylchalcogenolate complexes of lead(II): Synthesis, structures and their conversion into lead chalcogenide nanoparticles

The reactions of Pb(OAc)₂·3H₂O with NaER yield homoleptic colorless to yellow complexes of composition, [Pb(ER)₂] (ER = SCH₂CH₂NMe₂ (1), SeCH₂CH₂NMe₂ (2) and SeCH₂CH₂COOMe (3)). These complexes were characterized by elemental analyses, UV–Vis and ¹H NMR data. Molecular structures of [Pb(ECH₂CH₂NMe₂)₂] (E = S or Se) have been established by single crystal X-ray diffraction analyses. These molecules have a distorted trigonal bipyramidal configuration around lead with the nitrogen atoms of the chelating chalcogenolate ligands occupying the axial positions. Thermal behavior of these complexes was studied by TG analysis. Pyrolysis in a furnace or in HDA (hexadecylamine) gave PbE nanoparticles which were characterized by UV–Vis, photoluminescence, XRD, EDAX, and TEM measurements.     

Fluoro-olefin chemistry Part 20 [1]. Reaction of hexafluoropropene with alcohols

Reaction of hexafluoropropene (HFP) with a series of alcohols under thermal, photochemical or peroxide-initiated conditions affords the 1:1 adducts CF₃CHFCF₂CR¹R²OH (R¹ = H, R² = H, Me, Prⁿ or CF₃; R¹ = Me, R² = Me or Et) in high yield via a radical chain mechanism. Adduct are not formed with the alcohols (CF₃)₂CHOH and CF₃CHFCF₂CH₂OH. Other 1:1 adducts of structure CHF₂CF(CF₃)CH₂OH and CH₃(C₂H₃CF₂CHFCF₃)CH₂OH are formed as minor products in the methanol and $\text{n}$-butanol reactions, respectively.     

Fluorinated phosphorus compounds: Part 6. The synthesis of bis(fluoroalkyl) phosphites and bis(fluoroalkyl) phosphorohalidates

Reaction of phosphorus trichloride with tert-butanol and fluoroalcohols gave bis(fluoroalkyl) phosphites (R_FO)₂P(O)H in 42-89% yield, where R_F=HCF₂CH₂, H(CF₂)₂CH₂, H(CF₂)₄CH₂, CF₃CH₂, C₂F₅CH₂, C₃F₇CH₂, (CF₃)₂CH, (FCH₂)₂CH, CF₃(CH₃)₂C, (CF₃)₂CH₃C, CF₃CH₂CH₂, C₄F₉CH₂CH₂ and C₆F₁₃CH₂CH₂. Treatment of these with chlorine in dichloromethane gave the bis(fluoroalkyl) phosphorochloridates (R_FO)₂P(O)Cl in 49-96% yield. The chloridate (CF₃CH₂O)₂P(O)Cl was isolated in much lower yield from the interaction of thionyl chloride with bis(trifluoroethyl) phosphite. Heating the latter in dichloromethane with potassium fluoride and a catalytic amount of trifluoroacetic acid gave the corresponding fluoridate (CF₃CH₂O)₂P(O)F in 84% yield. Treatment of bis(trifluoroethyl) phosphite with bromine or iodine gave the bromidate (CF₃CH₂O)₂P(O)Br and iodidate (CF₃CH₂O)₂P(O)I in 51 and 46% yield, respectively. The iodidate is the first dialkyl phosphoroiodidate to have been isolated and characterised properly—its discovery lags behind the first isolation of a dialkyl phosphorochloridate by over 130 years. The fluoroalkyl phosphoryl compounds are generally more stable than known unfluorinated counterparts.     

单氢钌配合物与水和2,2,2-三氟乙醇的作用机理

利用原位¹H和³¹P NMR对单氢钌配合物TpRu(PPh₃)(CH₃CN)H [Tp＝hydrotris(pyrazolyl)borate]与H₂O和酸性HOCH₂CF₃的反应进行了研究, 结果显示相应的反应产物分别是TpRu(PPh₃)(CH₃CN)(OH) 和TpRu(PPh₃)(CH₃CN)(OCH₂CF₃). 观察到反应过程中Ru-H…HOH和Ru-H…HOCH₂CF₃分子间的氢键作用. 提出了生成TpRu(PPh₃)(CH₃CN)(OH)和TpRu(PPh₃)(CH₃CN)(OCH₂CF₃)的不同作用机理. 在水存在下, TpRu(PPh₃)(CH₃CN)H 与H₂O反应, 经过中间体TpRu(PPh₃)(H₂O)H和TpRu(PPh₃)(OH)(η²-H₂)生成产物TpRu(PPh₃)(CH₃CN)(OH). 而TpRu(PPh₃)(CH₃CN)H与酸性HOCH₂CF₃反应时, 单氢配体被质子化形成中间体[TpRu(PPh₃)(CH₃CN)- (η²-H₂)](OCH₂CF₃), 进而转变成产物TpRu(PPh₃)(CH₃CN)(OCH₂CF₃). TpRu(PPh₃)(CH₃CN)(OCH₂CF₃)与H₂作用, 经中间体TpRu(PPh₃)(HOCH₂CF₃)H生成TpRu(PPh₃)(η²-H₂)H.     

Fluorinated peroxides derived from hexafluoroacetone. II. Insertion of (CF3) 2CO into alkali-metal peroxides and subsequent reaction with active halogen compounds

The novel alkali metal peroxide derivatives (CH₃) ₃COOC(CF₃) ₂ONa, NaOC(CF₃) ₂OOC(CF₃) ₂ONa and CF₃C(O) OOC(CF₃) ₂ONa have been prepared through reactions of hexafluoroacetone, (CF₃) ₂CO, with the sodium salts of various organic hydroperoxides. These new salts are soluble in water and polar organic solvents and have been used to prepare the new covalent fluorocarbon/hydrocarbon peroxides [(CH₃₃COOC(CF₃) ₂OC(O)C₆H₅, (CH₃) ₃SiOC(CF₃) _2-OOC(CF₃) ₂OSi(CH₃) ₃, and (CH₃₃COOC(CF₃) ₂C(O)CF₃] through reaction with compounds having active halogen. Although the new peroxides are apparently less flammable and explosive than their hydrocarbon analogs, they also exhibit shorter half-lives than the parent compound (i.e., the peroxide without hexafluoroacetone insertion).     

Surface properties and structure of organofluorosilicon polymers based on organotrialkoxysilanes R<Superscript>F</Superscript>OCH<Subscript>2</Subscript>Si(OR<Superscript>F</Superscript>)<Subscript>3</Subscript>

The hydrolysis of trifunctional alkoxysilanes R^FOCH₂ Si(OR^F)₃, where R^F = CH₂CF₃, CH₂CF₂CF₃, CH₂CF₂CF₂CF₃, or CH₂CF₂CF₂CF₂CF₃, during the action of atmospheric moisture in the presence of 3-aminopropyltriethoxysilane under mild conditions yields new ladderlike polysiloxanes. Their structure is studied via ¹H NMR spectroscopy, GPC, TGA, and AFM. Polymer coatings prepared on their basis are found to be low-energy and hydrophobic. The total surface energy and polarity of the surface of polysiloxane films decrease, while their hydrophobicity increases with lengthening of the fluoroorganic substituent at the silicon atom.     

A mass spectral study of some symmetric and unsymmetric sulfides,disulfanes, and trisulfanes

The low-resolution mass spectra of 13 trifluoromethyl and/or methyl sulfur-containing compounds (CF₃S_nCF₃, CF₃S_nCH₃, CH₃S_nCH₃, CF₃S_mCl, and CH₃S_mCl; n = 1, 2, 3; m = 1, 2) are reported and discussed. There is a considerable similarity between the fragmentation pattern of compounds with the same terminal groups. However, with a fluorinated and a non-fluorinated methyl group, the major fragmentation products produced are similar to those for the dimethyl compounds.     

Ab initio and RRKM calculations for the reaction channels of O(1D) + CH3CHF2

Ab initio and Rice–Ramsperger–Kassel–Marcus theories are carried out to study the potential energy surface and the energy‐dependent rate constants and branching ratios of the products for O(¹D) + CH₃CHF₂ reaction. Optimized geometries and vibrational frequencies have been obtained by MP2/6‐311G(d,p) method. The main products of the title reaction are CH₃CFO + HF, CH₂CFOH + HF, and CH₃ + CF₂OH at lower collision energy; and CH₃ + CF₂OH, CH₃CF₂ + OH are the main products at higher collision energy. CHF₂ + CH₂OH are the main products in the whole range of collision energy. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2012     

Preparation and reactions of trifluoromethyl-sulfur oxide nitride

In the reaction of CF₃SOCl with NaN₃ or (CH₃)₃SiN₃, azide, CF₃SON₃ (I) is formed:

Upon gentle warming to room temperature, (I) decomposes under evolution of N₂ to give CF₃SON (II),

which however oligomerizes instantaneously, The monomeric nitride(II) can be captured in the presence of reactive halogene compounds to yield N-substituted trifluoromethan-imino sulfonyl chlorides. With CH₃CN, a six-membered ring compound is obtained: